Questions worth asking

Buying a condo or in an HOA? Skip to those questions ↓

When touring & buying any home

• How old are the roof, furnace, A/C, and water heater?The big-ticket items. Each has a known lifespan, a 22-year-old furnace isn't a dealbreaker, but it belongs in your math.
• Any history of water in the basement or drainage issues?Chicago basements and water have a long relationship. Look for efflorescence, fresh paint on foundation walls, and ask directly, sellers must disclose known issues.
• What's the electrical service, and is any old wiring left?100-amp minimum for modern living; ask about knob-and-tube or aluminum wiring in vintage homes, both affect insurance and lending.
• Has the sewer line ever been scoped or rodded?A $300 sewer scope during inspection can save you a five-figure surprise, especially with mature trees out front.
• Why is the seller moving, and how long have they owned it?Motivation shapes negotiation. A relocation deadline reads differently than a casual test of the market.
• How long on market, and any price history?Days on market plus price cuts tell you how much leverage you have before you write a number.
• What are the real utility costs?Ask for actual bills, a charming vintage home with radiator heat can run triple the gas bill of a newer build.
• Were the renovations permitted?Unpermitted work can surface at appraisal, insurance, or resale. City of Chicago permits are searchable, we check as a matter of course.
• What are the property taxes, and which exemptions are applied?A senior freeze or senior exemption vanishes when you buy, the real bill can jump sharply from what's advertised.
• What stays with the home?Appliances, window treatments, TV mounts, the EV charger, get it in Paragraph 7 of the contract, not in a conversation.
• Visit at different times.Not a question, but the best diligence there is: rush hour, Friday night, Sunday morning. Trains, flight paths, and the bar on the corner all keep different schedules.

When buying a condo or HOA property

• What's the monthly assessment, and what does it include?Heat, water, internet, parking, inclusions vary wildly and change the real monthly cost comparison between buildings.
• Any special assessments, pending, proposed, or being discussed?The classic condo trap. Confirmed ones before acceptance are the seller's; ask what the board has been *talking* about, then verify in the minutes.
• How healthy is the reserve fund?Reserves are the building's savings account. Thin reserves plus an aging roof or facade equals a future special assessment with your name on it.
• What are the rental restrictions, and what's the current rental percentage?Rental caps affect your exit options and investors' interest; high rental percentages can complicate conventional financing.
• Is the association involved in any litigation?Lawsuits can freeze lending in a building entirely. This must be disclosed, ask early, not at the closing table.
• What major building projects are coming?Roof, elevator, tuckpointing, and Chicago's facade ordinance inspections are shared costs. Ask what's been done recently and what's next.
• Professionally managed or self-managed?Neither is automatically better, but self-managed buildings live and die by their volunteer board, read the minutes for how functional it is.
• What insurance does the association carry, and what must I carry?The master policy covers the building; you'll need an HO-6 policy for your unit's interior, and the deductible structure matters.
• Is parking deeded, limited common element, or assigned?Deeded parking is yours and appears on the deed; assigned spaces can be shuffled. It's also a resale value question.
• What are the rules I'd feel?Pet limits, grill policies, move-in fees and elevator reservations, short-term rental bans, the small print that shapes daily life.
• Can I see a year of board minutes?The single most revealing condo document: what the building argues about, what's breaking, and what's brewing, all in one place.