Unless of course he is betting on appreciation or can substantially increase income or slash expenses.

I bet within a hour and 1/2 drive there are deals that will cash flow nicely.

It has the potential to net around 15% cash on cash IF I can refi it at around current market rates in a year or two, if not, it’ll be more like 6% (which, sadly, is pretty standard for the area) until inflation pushes rents up.Would you bet on this thing?

Take a similar approach and engage with them....again within reason.90% of the time, if not more I bet these people deal with angry, rude, impatient and unreasonable citizens who are mad at them for a citation or just because they exist.

But, investing in what you know and generating better returns with a safer underlying asset is definitely a good reason to consider holding rentals, being a hard money lender or even flipping houses within an IRA or Solo 401k.

The better areas of Chicago just like the better real estate markets of the nation have quickly bounced back towards peak prices, so the equity bet is risky.  

Your best bet is to crash on someone's couch until you have a job then start hunting for your own place.

Generally your safest bet would be to simply pay off the HOA to protect yourself. 

I'll bet you know a good lawn service who would work with you and do it for free or greatly reduced in exchange for the chance to get a long term client.  

I bet there's a house already for sale in the same area as your theoretical acreage, for $60k.