If the prior landlords confirm he was fine, I'd rent to him. 

You are in a fine spot financially, at least from what you shared.

Simply scroll to the bottom and you can actually interact with clients like @Bill B. who have direct experience working with that QI.If you have a comfort level working with someone local that is perfectly fine. 

I would only hire out for major work I can't do myself or emergency repairs.I've dealt with older houses before and the house may be fine for occupants but there's still usually lots of things that can be fixed / improved so it seems a house that isn't perfect would give more opportunities for ongoing maintenance of this sort.To me it seems fairly straightforward to meet the time requirements but I think I need to have extensive documentation?

@Daniel Curtin Blue Island will be fine as long as you have a strong plan for management.

Ong: I apologize and I think I have to rephrase: I do understand I have to work for a few years, that I'm fine with.

If you live in Ashland, KY, there is really no reason to buy 2 duplexes out of state since the numbers near you will be fine.

Anything you do is fine since the objective is not higher return.  

They tend to look at the bigger picture rather than just the fine print.

If you click the photo it should open full size in another tab.)This is imprecise so you can take this and fine tune it to make it better, but you get the idea.