Fortunately, I have a natural tendency to do the right thing and in a timely manner so his complaints to have "safety" issues addressed are not too much of an inconvenience for me (although the renter himself is an annoyance). 

Bates-Hendricks and Arsenal Heights are real close to FS so it seems a natural bet that one or both areas will change in a similar way--they might-- but my hunch is it will take several years for market appreciation in those areas. 

What is an adequate Cap rate for a 14m dollar project?

@Thomas S. why you say never count on staying in any home forever ( unless of course it is related to natural disasters striking and destroying your home ) ...

Renovating a C will not produce adequate returns to justify the effort.

That's not a common nor natural leap of thought. 

This isn't as big of a problem if the building is adequately cash-flowing and you have minimal value-add rehab.

. $300/monthGrass/snow - quoted by a local company at $274/month (1800 for snow for the year, 1500 for grass for the year) Insurance - $140/month (got a great rate not cheap insurance) The heat source and hot water is natural gas, New furnaces and water heaters installed in 2015. 

I completely understand where you’re saying wear and tear exists, but I think it’s probably unlikely that ANY landlord could expect the place to be in perfect shape when the tenant arrives and leaves, natural wear and tear is going to happen.

A mentor will probably COME NATURALLY at some point if you really focus on networking.