Chicago real estate buy / rent

Currently looking at buying a condo in Chicago but am not convinced it's the right move. Looking through Zillow it seems there is a ton of supply, and the price histories don't show a ton of appreciation over time. This coupled with recent outflows of large companies has me wanting to continue renting, as I could see many more properties come on the market over the next few years. I'm tempted to buy a place in Florida as a vacation home, and continue to rent in Chicago.

Thoughts / experiences?

10 Comments
 

I'm renting in Chicago currently with a plan to get a condo/town house in west loop in a couple years. It's crazy right now, I was touring here and there this summer and every place is 95% occupied. Having a Florida vacation home is a solid idea. Personally, I was looking at Wellington area as they have the big equestrian hub there with many opportunities to rent out a place during polo season. It's about 25-30 mins from Palm Beach and 1hr 15 from Miami. 

 

Just need to use your best judgement honestly. What is your time horizon? Condos in high rises typically don’t see a lot of price appreciation. I’ve owned my condo since 2019 and although I’m not expecting to see a ton of price appreciation when I sell next year, it is nice to see that my home equity has grown and I can take that with me to my next home. Plus there’s the comfort that my mortgage is a fixed cost and I’m not at the mercy of a landlord jacking up rent.

 

But at the same time, your RE taxes are not a fixed cost - how have you seen these change during the past couple years?

 

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