Is it good year to purchase a 2 BR condo in Chicago or does it make sense to wait for an extra year or two? Hard to predict the RE market for next 2-5y.

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Do you have enough cash for at least 20% down payment? And can you afford the monthly payment that includes P&I, home insurance, property tax, and HOA fee? If so then yeah. Nobody can predict the market

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If youre a long term investor the market performance over the next 5yr doesn’t matter much

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Good point

P1 hit the nail on the head. Location location location. Plus, it’s a buyers market right now. We’re selling our condo right now and it’s crazy how in control the buyers are. Offers are coming in at 10% below ask and expectations are to meet somewhere in the middle. If you can do it, now is a good time to flex

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What would you consider desired locations now? Neighborhoods where people wish to live (West Loop, LP, River North, Wicker) or neighborhoods with potential (South Loop, Logan Square, Pilsen)?

Market is softening across the US, and probably going to continue. Don't forget being a homeowner also means fixing broken crap and replacing appliances, stuff you don't have to worry about when you rent. I think people don't do enough of an analysis around renting vs buying and get hung up on "giving away out money in rent", then they get a huge mortgage and have to remodel the kitchen, fix the toilet, buy a new fridge, etc and they get caught up in tons of debt. If you're not putting at least 40% down, you could end up under water in a downturn, which matters if you have a huge mortgage and then need a second to pay for the burst pipe and realize you may just need to sell. Point is, don't assume buying is the ,"smart thing", plus deducting your interest/taxes is now nowhere as good a deal as it used to be .

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If you are going to live there for at least 5plus years, now is as good a time as any. Interest rates are reasonable. Watch out for the tax bills and be sure to factor that in, as well as future increases in the monthly condo fee.
You will probably be better off than if renting but stay within your means!
Oh yes, don’t forget Location, Location, Location drives value

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In Chicago, in long run probably only going to keep pace with inflation....dont see what will drive positive real returns. Demographic trends don't bode well for the city or state. Illinois will also be the state leading the way when public employee pension funds go bust. All depends on what you pay, but in short, opportunity cost of buying now or anytime in next few years is probably negative

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