Its an actual health problem from what you describe, not just a theoretical burden.

@Dave Godfrey  I've been on the contractor side of several JV deals just like you are describing. 

What you're describing is a gross lease, not single net.

Realtor's operate under a stringent set of licensing and ethics requirements - doing what you describe would be grounds for having their real estate license revoked.3) No - you need an "or assigns" clause in the original contract, so this is something you would want to do in advance, not afterwards.

In the scenario you describe, you would be paying income tax on the rental income, assuming it is positive.

I let the tenant describe damage and we take pictures of anything noted.

It's a great combination of networking to meet all of the ppl you described, education (talking about Opportunity Zone investing tomorrow) and there are a ton of vendors, including lenders.

I've heard it described this way: if you want to keep hot air inside a balloon what would you do first, wrap it in fluffy stuff or tie off the end?

Everything you just described is pretty normal for Chicago.

I think it's perfectly reasonable to lease an apt sight-unseen in the situation as described.