When I looked at prices recently they look like they've gone up quite a bit but I know they vary a lot depending on the neighborhood. 

Solar panels and backup battery system installed in 2022, I have a loan for the system so that would eat into any sales.I'm in San Antonio, Tx.

Quite frankly, if I were in your shoes I would try to get one of my siblings to buy me out and then invest that 40k somewhere else.

Do you eat out for lunch every day, get coffee twice a day, have a new fancy car, and buy the latest trends?  

There are opportunities out there but some strategies are risky. 1 - Airbnb (STR) comes to mind - very competitive, very saturated and becoming highly regulated.2 - Most STRs are transitioning to MTR so that market will be saturated soon if it isn't already.3 - Insurance crisis in florida is getting bad so those costs will eat up cashflow and short term appreciation.

We eat the first one, thy get a picture of all the glory the plumber pulled out and the second time they get billed.

. - You've got some pretty solid information above and concurrence that it shouldn't cost nearly as much as you thought, but on a separate note, I'd like to understand your situation a bit better.You are currently just looking for a Chicago property to purchase and asking the quit claim question in preparation for closing? 

That kitchen looks good but needs more stuff so families can cook and eat there.I think you guy look good in the photos, but it can be a turn off to prospective guests so I would remove those.

Condo's usually have high HOA dues which will eat into your cash flow.

I had to live in the property due to the FHA occupancy rules, so I had about an hour and 15 minute commute to work every day.I settled on Tilton (small town in central NH) because the property was right and it cash flowed very well, and was quite cheap (at the time... 240k), I could get the loan to get into the building and own 4 units.