I had recently just refinanced our two-flat to get out of the PMI using a major, big name bank.

Population growth is flat, as well as income. 

When the other lease is up you should be able to raise rent even in a market with flat rents because you have addressed the deferred maintenance.  

The association consists of 3 12 flats, so 36 total units. 22 of them are rented.

Which is maybe the most appealing part of the plan.So, shoot holes in my half baked plan please so I can move to something else.

So the 14th i got a call from another tenant, (its a 4 flat) say there was water coming from in basement coming from that unit.So i tried calling him telling him I was coming to check it out.

So if expenses are flat (which they won’t be) you “only lose $40K per year”.It’s been on the market over 12 months.

Are they going up, down, staying flat?

I've found this real estate agency in Alicante offering pretty cheap flats. 

I'm looking to house hack my first property, and I'm not sure if I should find a 2 or 3 flat in Chicago area where it's more expensive and what I can afford will definitely need more work then I would like, or buy a multifamily property is a suburb where I can find a property in better shape and perhaps at a lower price with a lower mortgage .