But the kind of tenant who will let things go all the way to eviction court, probably doesn't care about that. 

If he doesn’t like it, go on to the next wholesaler.

It's a given that it would cost more than the same trip via a ground car, even if ground transportation doesn't gain its own improvements (which it will - autonomous networked vehicles will make the ground trip safer, faster, and cheaper than present ground transit, and that is *much* closer to a broad implementation than air taxis). 

However, if He doesn't have sufficient income to qualify - there aren't any banks that will lend him the money. 

Therefore he doesn’t use any of his contacts that are also making him money.

You guys might be a little quick on the trigger here;  in many, if not most, jurisdictions an owner can pull permits/function as a GC Only on an owner occupied property, not as an investor/flipper, and usually requires the owner to retain the home for at least a year before selling/renting, to qualify for that exemption.While the OP may indeed need a new accountant, he doesn't even know what kind of license the accountant was referring to, apparently he didn't even ask.

You need a condo with a low monthly assessment and West Loop doesn't have many options. 

The tax assessor's site doesn't list half of what I want so I'm hoping there is another way.Thanks in advance!

It doesn’t look like they serve my area of CT, but I’ll check with them just in case.

Tried Brian he doesn't have experience on the other side with lenders, thank you