If you already have a solid team in place with your first property adding a second should be fairly easy.

He is 44, lives alone, has a landscaping business that is doing fairly well.  

But I'm still fairly new to MTR/STR so I'm learning as I go.

If so, why not partner with someone else that can help you fund the deal, either 100% or have your money partner fund 20% and a commercial bank fund 80% then flip it and split the profits w/ your money partner at whatever split you all think is most fair? 

Is it fair?

I'll then list my properties on the high end of whatever I think fair market rent is.

Per fair housing regulations, I can't answer this question. 

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?

Some fair criticism for sure.

Fair point!