The biggest question I would ask is how well they know the area such as neighborhoods and do they have connections to building a CORE 4 such as great contractors, property managers, attorneys, etc

If you had also spend money on renovations and improvements while occupying those should have gone into service then as well. 

I'd love feedback and advice from those of you who are well ahead of me.

I enjoyed working with you as well.

I think they can go very well if done right or poorly if not, and right.Here or a couple of suggestions. 

Are you thinking about managing versus a property manager or are you also thinking of selling as well?

A well written management contract should clearly spell out what is expected of both the PMC and the owner, to PROTECT both and avoid misunderstandings.

I've done this with my properties because I'm well known in my small town and don't want people to know what I own.

Well if you think the guys hanging out at home depot are contractors .

If you like the neighborhood, chances are other people will want to live there as well.