Just to close the loop here, I received reliable counsel that you should, indeed, use in-State Land Trusts.  

You need good, reliable, trustworthy contractors and a fantastic real estate agent that understands the real estate investment business.

It's not your local neighborhood and it'll take time to get to know a metro and build up a reliable team.

Very reliable when installed and left alone.

I have a plumber who is doing a job at my Cicero property, and I am happy to make the introduction if you need a reliable guy to take a look.

Can someone recommend good, reliable contractors?

It's hard enough to find a licensed and insured contractor who is great at their job and reliable, never mind if you started hiring handymen.Just like filtering tenants who don't meet your criteria I recommend you implementing finding licensed, and insured contractors as a filter to make your life easier long-term. 

I think the most reliable contingency to get out without a scratch is inspection contingency, isn’t it?

You could also employ an agent to do this for you, but it would be a CMA, not an appraisal, and not as reliable, depending on the agent.* All other properties in the neighborhood are 1 level.

I can reliably make ~15% returns by investing in real estate.Given how much debt you have and your current living situation, I would split the difference.