Can you share any high level details about the nature of the trickiness so we can also help others learn on this thread?

This leaves the tenants extremely frustrated, especially if it's a refrigerator issue causing their food to spoil, or possibly an issue with an appliance leaking water onto the floor, etc. 

This tenant has been a pain in the *** and high maintenance from the get go, but we are stuck with them.  

Hello Galen, I would highly suggest not trying to get super creative here and just form your own LLC, buy the property and put it in there, and write this one off as a win! 

I honestly should have more money saved up considering my years of working full-time, however younger financial mistakes have been a painful lesson and I regret not purchasing a property sooner/younger.My most important and immediate goal right now is to purchase a property.I am in (what I perceive to be) a relatively high cost real estate area. 

But because of high prices and high rates most of the properties seem to be breakeven (at best), so this may be something to look into once rates decrease.

@Nick BednarczykI think people also need to understand that fed rates are not directly correlated to mortgage ratesMortgage rates are more in line with the 10 year treasury which could remain high if we continue to spend money like a drunken sailor

The two downsides to syndications are the high minimum investment and the difficulty in finding good sponsors and deals, but you can solve for both by joining a passive real estate investment club.

Check out this on their site, if you think 50th percentile pricing is too high, you may want to try pricing at 25% and see how that looks.  

There is both great cash flow and appreciation markets within ChicagoNow with all that said Chicago FOR SURE has it's challenges, but I have found personally that if I lean on #1, my network, that a lot of those high risks go away or can at least be mitigated.