Best time to sell an HOA condo in Chicago, IL

[Dima DeSimone]

Hello community, love all the topic and discussions. My story below and pls don't hesitate to advice, comment, share and critique. TIA

Bought an HOA condo in Lakeview in 2005 for $160K with the LT plan to leave it as an investment property. With the 2008 downturn, HOA changed bylaws and grandfathered rentals to 30%, where new rentals can only do it for 2 yr, therefore not worth it even if you ever clear the wait list.

I have decided to sell as there is no other options for me, as well as a nasty self managed HOA. The property does not serve my needs as owner occupied any more.

My main concern is how overheated the market in Chicago is and when we can start seeing prices go down or inventory too high. Overall I would like to list it and I am not sure when. I will be losing money, that's 100%:(. What do you guys think of the Chicago market as of now, would waiting till spring be worth it and ok, what would you expect the markets to do? Pls share with me as I truly need some advice. Thanks again!!!