North port is a great growing market, and I would expect that you will do very well on your first property. 

@Travis TimmonsI had the same reaction as you did, but I held off on posting since I don't yet invest in STRs (I'm all LTR so far, and looking into my first MTR).Buying an STR "to offset income" makes me nervous as well...

Other lease provisions may apply as well, such as prohibition against causing the LL to incur fines and damages.

The alternative to that is going to the Cape, Western MA, as well as adjacent states with coastal/lakeside properties where many of us New Englanders vacation. 

So I would like to get these things hashed out well beforehand as something to present to potential clients and have procedures for my company.

I work with investors in Huntsville, and there are big things heating up here, as well.

Any good HML will be happy to share the contact info of borrowers so you can see how easy the process was and how well they treated the investor.Can you share a recent closing document or HUD?

I called my local insurance company, as well as two major companies and was told "good luck." 

(Could be more than just two) So just be aware, you can use the sec 8 income to help with qualifying for a DSCR loan but you could very well end up with a higher rate.  

Locations that are a 0-1 hour car ride from san juan to a nice town/city with more affordable areas walking distance to the beach would be interesting as well.