Most first-time buyers don't lose deals because they picked the wrong house. They lose them because nobody explained the process before it started moving. This is that explanation — every step, every deadline, and the questions you don't yet know to ask.
You will not remember all of this on the first pass — and you don't need to. What matters is that when your attorney says "we're clear of attorney review" or your lender asks for an updated bank statement on day 22, you already know where that fits.
The gold circles throughout are the questions almost nobody asks until it's too late. Open them.
Before a single showing. This phase decides what you can buy, how fast you can move, and whether a seller takes you seriously.
These two words get used interchangeably and they are not the same thing. A pre-qualification is a conversation: you tell a lender what you make, they tell you a number. It's worth almost nothing in a competitive offer. A pre-approval means the lender has pulled your credit, reviewed your actual income documents and assets, and issued a written commitment subject to the property.
In a multiple-offer situation, a listing agent is reading your pre-approval letter to decide whether your offer is real. A soft letter gets you beaten by an identical offer with a stronger one.
No — and you should shop. Credit scoring models treat multiple mortgage inquiries inside a short window as a single event, because they assume you're rate shopping rather than opening five mortgages. The window is typically 14 to 45 days depending on the scoring model in use.
Get at least three quotes: a big bank, a local credit union, and an independent mortgage broker. Compare the interest rate and the lender fees side by side — the rate is only half the cost. Two lenders quoting the same rate can differ by thousands in origination and processing fees.
Because a lender is underwriting your ability to repay, not your quality of life. They see gross income and required debt payments. They do not see your 401(k) contribution, your travel, your daycare, or what you'd like to save each month.
Take the approval number as a ceiling, not a target. Decide your own comfortable monthly payment first, then work backwards to a price. That number — not the approval — is what we shop with.
The single biggest myth in buying is that you need 20% down. You don't. Conventional loans go as low as 3% down for qualified first-time buyers, and FHA loans go to 3.5%. What 20% actually buys you is the elimination of mortgage insurance.
But down payment is only one of four buckets. The full cash requirement is: down payment + closing costs + earnest money (which credits back to you) + reserves the lender wants to see you keep after closing.
Very possibly. The Illinois Housing Development Authority (IHDA) runs a family of programs offering roughly $6,000 to $15,000 in assistance — some deferred until you sell or refinance, some forgiven over time, some repaid monthly at zero interest. They generally require a minimum 640 credit score, a pre-purchase homebuyer education course, and compliance with income and purchase-price limits that vary by county.
Two things matter here: the terms and limits are updated periodically, so they must be confirmed with a participating lender at the time you apply — and not every lender is approved to originate them. Ask your lender directly whether they do IHDA loans. If they say no, that's a reason to talk to another lender before you commit.
On a conventional loan, private mortgage insurance (PMI) is not permanent. It can generally be removed once you reach 20% equity, and it is required to terminate automatically at 78% loan-to-value based on the original amortization schedule. Rising values or improvements can get you there faster than the schedule — you request a new appraisal and ask for removal.
FHA is different and this is the part people miss: on most FHA loans made with the minimum down payment, the mortgage insurance premium lasts the life of the loan. Removing it means refinancing. That doesn't make FHA a bad choice — it makes it a decision you should make deliberately rather than by default.
As of August 2024, this is not optional. Any agent who is an MLS participant must have a written agreement with you before touring a home — in person or by live video. If an agent offers to show you property without one, they are out of compliance, and that tells you something.
The agreement has to state the compensation clearly and objectively — a specific amount or rate, not open-ended language like "whatever the seller is offering." You must also be told plainly that commissions are not set by law and are fully negotiable; that disclosure may appear in the agreement itself or alongside it. Read those lines. Ask about them.
In practice, almost never — and the mechanism is built right into the paperwork. Your agreement with me establishes what I'm paid. Then, on the first page of the purchase contract itself, there is a section stating that the seller is to cover that fee. It's part of the offer you submit, negotiated alongside price and terms.
That means it is settled before you ever have an accepted offer — never a surprise discovered later. If a particular seller pushes back, you know it while we're still negotiating, and it becomes a lever like any other. In my transactions this has been covered by the seller roughly 99% of the time.
Illinois law does not require you to hire an attorney to buy a home. But in Chicago, essentially everyone does — an attorney is a normal, expected part of every residential transaction here, on both sides. They review and modify the contract, handle title, and represent you at closing. Going without one in this market would put you at a real disadvantage against a seller who has one.
Have yours identified before you write an offer, not scrambling after acceptance with a five-business-day clock already running.
This is the part everyone pictures. It's also the part where the wrong criteria quietly cost you months.
Every buyer arrives with a list. The useful exercise is sorting it into three columns: non-negotiable, strongly preferred, and would be nice. Then we test it against real inventory in your price range. Sometimes the list survives intact. More often we find that two items on it are in direct conflict, and knowing that early saves a season of frustration.
Things that are permanent: location, layout, light, view, floor, noise exposure, parking. Things that are not: finishes, paint, appliances, fixtures. Buyers routinely overweight the second list.
You're choosing how much of the building you're responsible for. In a condo you own your unit and share ownership of everything else — roof, façade, elevators, common areas — through the association, and you pay a monthly assessment toward that. In a single-family home there is no assessment and no board, but the roof is entirely your problem.
The mistake is comparing a condo's list price to a house's list price. Compare the total monthly cost: mortgage, taxes, insurance, and assessment. A condo with a low price and a high assessment can cost more per month than a house that looks more expensive on paper.
Whether it's deeded, and whether it's included. In Chicago, parking is frequently a separately deeded interest with its own price and its own tax bill — a unit advertised at one price may be quoted "plus parking" for an additional sum. Some buildings offer leased or assigned spots instead, which convey no ownership and can be reassigned.
Ask three questions on every unit: is the space deeded or leased, is it included in the list price, and does it carry a separate assessment. The answers change your monthly number and your eventual resale.
Showings blur together fast. By the sixth property, buyers start confusing which one had the good kitchen. We solve this by touring in tight clusters and debriefing immediately after each block, while it's fresh.
What I'm doing during a showing that you may not notice: checking the direction the windows face, listening for the L or highway noise, looking at the ceiling in the top-floor units for water staining, reading the hallway carpet and the mailroom for how the association actually spends money, and noting how long the unit has sat and what it last sold for.
More than the number itself. A property that's been sitting for 90 days in an active price band is usually telling you it's overpriced, has a condition issue, or has a building issue — and that's leverage. But watch for listings that were withdrawn and relisted to reset the clock: the days-on-market reads as new, and the actual history doesn't.
I pull the full listing history on anything you're serious about — prior list prices, prior expirations, prior contracts that fell through. A deal that died in attorney review twice is a signal worth having before you write.
Price is one of roughly eight levers. Buyers who only pull the price lever lose to buyers who understand the rest.
Before we write, I pull comparable sales and current competing inventory so the number is defensible — both to you and to the appraiser who will eventually have to support it. Then we set the terms.
Your three inspection choices. These get collapsed into "inspection or no inspection" all the time, and they are not the same thing:
Your earnest money, and sometimes more. Contingencies are the doors out of the contract, and each one you close narrows your exit.
Waiving the inspection means no inspection happens at all. You lose the ability to cancel over a problem that an inspection would have surfaced — because nobody ever surfaced it. On a hundred-year-old Chicago building, that is a meaningful bet.
Waiving the mortgage contingency means that if your loan dies, you are in breach. Your earnest money is at risk and, in principle, so is a claim for damages.
There are situations where a targeted concession is the right call — and there are ways to strengthen an offer that carry far less exposure: inspecting without requests instead of waiving outright, a larger earnest deposit, an escalation clause, appraisal gap coverage, or a closing date built entirely around the seller's timeline. We choose deliberately. I will tell you plainly which risks I think are worth taking and which aren't.
The lender will only lend against the appraised value, not your contract price. If you're under contract at $420,000 and it appraises at $405,000, that $15,000 gap has to be resolved — the seller reduces, you bring the difference in cash, you meet somewhere in between, or the deal terminates under the relevant contingency.
This is why "appraisal gap coverage" appears in competitive offers: you commit in advance to covering a stated amount of any shortfall. It's a real strengthener, and it's real money. Only offer what you actually have available beyond your down payment and closing costs.
A seller can accept, reject, or counter. Countering is normal and is not a rejection. What matters is that we stay on top of every response window, because in a competitive situation the buyer who responds in two hours often beats the buyer who responds in two days at the same price.
When both parties have signed, you are under contract — and the clock on every deadline in the document starts running.
Not quite, and this is one of the genuine advantages of buying in Illinois. See the next step.
Thirty to forty-five days of overlapping deadlines. This is where deals are actually won and lost, and where having someone tracking every date matters most.
This is the Illinois advantage and most first-time buyers have never heard of it. For a defined window — five business days under the standard Multi-Board contract used across Chicagoland, counted Monday through Friday and excluding federal holidays — your attorney can propose modifications to the agreement. Attorneys negotiate in writing, usually by email, and the contract does not become fully binding until the period resolves.
Worth knowing: this window comes from the contract form, not from a statute. It can be shortened, lengthened, or negotiated away — which is one more reason the specific document you sign matters.
Commonly modified in this window: inspection contingency mechanics and deadlines, financing contingency language, title requirements, the closing date, earnest money terms, and exactly which fixtures and personal property convey.
The attorney review provision is meant for negotiating terms, not as a free look. Practice varies and your attorney will advise you on the specific language in your contract, but you should not go into a contract assuming you can exit for any reason during the window. Write offers you intend to close.
Your inspection window runs on the same clock as attorney review — the first five business days after acceptance, not a separate period afterward. That's why we book the inspector immediately rather than waiting to see how attorney review goes. The window can be extended by agreement, but you should plan on it being tight.
You hire the inspector; you attend if you can. A general inspection covers structure, roof, electrical, plumbing, HVAC, and visible moisture. Depending on what turns up, specialists follow — sewer camera, roof, structural, radon, mold, chimney.
The report will be long and it will look alarming. Nearly all of it is normal. My job is to sort it into three piles: safety and structural, expensive and near-term, and cosmetic and eventual. We negotiate on the first two.
A lot of this city was built before 1940, which is part of its appeal and part of what to inspect for. Things worth flagging to your inspector on an older building: knob-and-tube or aging electrical service, galvanized or lead supply lines, clay sewer lines with root intrusion, tuckpointing and façade condition, flat-roof drainage, and moisture in below-grade space.
None of these are automatic dealbreakers. All of them are things you want priced before you own them rather than discovered after.
If you're buying a condo in Illinois, the seller or association must provide a disclosure package under section 22.1 of the Condominium Property Act. This is the single most under-read document in the transaction, and it is where the expensive surprises live.
What's in it: the association budget and balance sheet, reserve fund balances and any reserve study, current assessment amounts and any pending special assessments, pending litigation involving the association, the declaration and bylaws including rental policy, insurance coverage and deductibles, and a statement of what the seller currently owes.
These don't all start on day one. The appraisal is typically ordered once attorney review has resolved — no lender wants to pay for one on a deal that might still fall apart over contract terms. Underwriting, title, and survey work generally get moving around the three-week mark and run in parallel from there. Any one of them can generate a request that needs a fast answer.
Because the search finds recorded problems, and title insurance covers the unrecorded ones — a forged signature decades back, an undisclosed heir, a clerical error in the chain of ownership, a lien that was never properly filed.
There are two policies. The lender's policy protects the lender's interest and you'll pay for it as part of closing costs. The owner's policy protects your equity, is usually paid by the seller in Illinois practice, and is the one that actually protects you. Confirm you're getting one.
The last ten days, and what happens after everyone stops paying attention.
"Clear to close" means underwriting is satisfied and the lender is prepared to fund. From there, three things happen in sequence.
In Illinois you'll sit at a table with your attorney and sign for roughly an hour. Bring government-issued photo ID. Your attorney reviews the settlement statement with you before you sign anything. When funds are disbursed and documents are recorded, you get the keys.
Then there are three things that most buyers don't get told, and they cost real money:
Move the sliders. This is an estimate built on typical Chicago figures — your actual numbers come from your lender and attorney — but it will get you within range and show you where the money goes.
Estimates only, for orientation. Assumes a 30-year fixed loan and typical Chicago cost ranges. Property tax is estimated from a general effective-rate assumption and will vary substantially by neighborhood, assessment, and exemptions; mortgage insurance is estimated and disappears above 20% down. Earnest money is not shown because it credits back to you at closing. Your lender's Loan Estimate and your attorney's settlement statement are the authoritative numbers.
These are customs, not rules. Every line here is negotiable, and what actually governs your deal is what the contract says.
| Item | Customarily paid by | Notes |
|---|---|---|
| City of Chicago transfer tax | Buyer | $3.75 per $500 — 0.75% of price |
| State & county transfer tax | Seller | $0.50 and $0.25 per $500 respectively |
| CTA portion, city transfer tax | Seller | $1.50 per $500 |
| Lender's title insurance | Buyer | Protects the lender, not you |
| Owner's title insurance | Seller | Local custom; protects your equity. Confirm it in the contract. |
| Survey | Negotiated | Often seller, but not fixed. Rarely required for condos. |
| Home inspection | Buyer | Paid at time of service |
| Appraisal | Buyer | Often collected up front by the lender |
| Attorney | Each side pays their own | Usually a flat fee |
| Condo 22.1 disclosure fee | Seller | Charged by the association |
| Property tax proration | Seller credits Buyer | Because Illinois taxes are paid in arrears |
A typical financed purchase closes in 30 to 45 days from acceptance. Here's what those days look like. Gold markers are the deadlines that actually bite.
Ordered by how often I actually see it. The first two account for most of them — and both happen in the first two weeks, which is exactly why those weeks get my full attention.
This is where most deals die. The report comes back, the buyer asks for repairs or a credit, the seller refuses or counters low, and neither side moves before the window closes. It is almost never the roof itself — it's two parties anchoring on numbers with a clock running. Going in with a clear sense of what you'd actually accept, before the report lands, is most of the fix.
The number two killer, and number one for condos. The 22.1 package arrives and it contains something real — a pending special assessment, thin reserves, active litigation, a rental cap that breaks the plan. Sometimes walking is the correct decision. What you don't want is to discover it after the window closed because nobody opened the file.
A financed sofa, a new car, a store card opened for the discount. Underwriting re-pulls credit before funding and a changed debt ratio can kill an approved loan days before closing. Buy nothing on credit until you have keys.
A large transfer from a relative without a documented gift letter and paper trail reads as an undisclosed loan to an underwriter. If someone is helping with your down payment, tell your lender before the money moves.
Inspection objections, condo document review, mortgage contingency. These expire quietly and on expiration your leverage — and sometimes your earnest money protection — is gone. This is what I track for you.
Conditions come in batches and each one stops the file until answered. Buyers who answer within hours close on time. Buyers who answer within days ask for extensions.
Criminals monitor real estate email and send convincing instructions at exactly the right moment. Always call a number you already had to verbally confirm before wiring. Wired funds are effectively unrecoverable.
Approved for the maximum and stretched from month one, with no room for a special assessment, a tax increase, or a water heater. The payment you're comfortable with should set the price — not the other way around.
A general inspector will recommend a sewer scope or a structural look. Those recommendations are not upsells. On older Chicago buildings they routinely find five-figure problems for a few hundred dollars.
Terms that will be used around you as if you already know them.
A good-faith deposit held in escrow after acceptance — commonly 1–5% on a Chicago resale, higher on new construction, always negotiable. Credited toward your purchase at closing, so it's not an extra cost — but it is at risk if you breach.
A condition that must be satisfied for the contract to proceed. Inspection, mortgage, and appraisal contingencies are your exit doors — each with a deadline.
The five-business-day window in Illinois during which attorneys negotiate contract modifications before the agreement becomes fully binding.
Two meanings. Funds held by a neutral third party before closing; and the account your lender uses after closing to collect and pay your taxes and insurance.
A standardized three-page disclosure of your rate, payment, and closing costs, issued shortly after application. Use it to compare lenders directly.
The final accounting of your loan and closing costs, delivered at least three business days before closing. Compare it to your Loan Estimate.
Protection against defects in the ownership history. The lender's policy protects the lender; the owner's policy protects you.
The difference when a property appraises below the contract price. Someone has to cover it — seller reduction, buyer cash, or a renegotiation.
A term that automatically raises your offer above competing bids by a set increment, up to a ceiling you choose. Useful in multiples — but some listing agents won't accept them.
Mortgage insurance charged when you put down less than 20%. Removable on conventional loans at 20% equity; typically permanent on most FHA loans.
The Illinois-required condo document package: budget, reserves, assessments, litigation, bylaws, and insurance. The most important reading in your file.
A one-time charge levied by a condo association for a major project beyond the reserves. Can reach five figures per unit. Check for pending ones.
Because Illinois taxes are paid in arrears, the seller credits you at closing for their period of ownership — calculated from the last bill at a negotiated multiplier, commonly 100–110%.
Underwriting has signed off and the lender is prepared to fund. The signal that closing will happen on schedule.
A Cook County property tax reduction for owner-occupants. You must file for it — it is not applied automatically after purchase.
Your monthly debt obligations divided by gross monthly income. The primary number underwriting uses to size your loan.
A parking space you own as a separate property interest, with its own price and tax bill — as opposed to a leased or assigned space you don't own.
That's the actual point of this document. Not to turn you into a transaction coordinator — but so that when a deadline lands or a report comes back or an attorney uses a phrase you haven't heard, you already have the context. Informed buyers make faster, better decisions, and faster, better decisions win deals.
Every deadline in here is one I'm tracking on your behalf. Every document is one I've read before you see it. Come back to this page at each stage — and bring me whatever it makes you want to ask.
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