Perhaps I can hire local MH dealer to sell the home, a RMLO to do what they need to do to stay compliant with Dodd-Frank & SAFE Act and still finance the sale to grow my smaller investment? 

with that cash flow I will stay away.

Commercial lending was still cake (even though I couldn’t refi my own home that I owned for 12 years l, never missed a payment, wasn’t looking to pull cash, etc)Tl:dr: stay away from 1-4 fam loans and you should be fine 

You know your location the best and irregardless of the numbers... you are collecting cash monthly and have the potential to make some large gains in 5 years - thats if the market stays in a decent place.  

So my question is, will this affect the appraisal in the future (lets act like the market will stay exactly where its at).

I am similarly in the same location dilemma for my next investment -- to stay in Chicagoland, or look to Wisconsin or Indiana for better opportunities. 

It would be in high demand for a week or two a year, but I wouldn't think many people would be looking to stay in that neck of the woods at an AirBnB outside of the week of Derby.

In the past, I've stayed away from partnerships because I have seen them go sour, however, I feel good about the current prospect and can see the value he brings to the table. 

Most of them I've seen marketed are way over-priced and I'd be curious to see how well the were rehabbed and how long the tenants stay and how long the properties actually perform. 

But I learned that the work really doesn't care who does it, as long as it gets done, and eventually I became a rather good handyman and parlayed that into DIY landlording as a way to break into the market here.If you're determined to stay in Boston, I cannot recommend getting out to local real estate associations and talking to other local investors highly enough.