Just like with a residential mortgage would they need business tax returns as well for add back purposes?

The length of holding only matters AFTER you already determined it was a capital transaction, as opposed to a flipping business.Step 1: business or investment?

Myself, significant other, and my close friend/business partner have been renovating his personal residence for the past few months with the intention of renting it soon.

My thought was also to just rent the lot itself as it's located on a pretty busy lake. 

CRedit Union or personal business line of credit at a lower interest rate would be best!

I never give out my contractors name for renovations because I keep him busy enough and he also has many other projects.

Again, that's all fine and good but the numbers have to work which is why I was hoping to speak to someone with first hand knowledge of owning a property or properties in the town without an axe to grind like the Seabrook sales people.On the issue of negative STR regulations roughly half the houses in the town are in their rental program currently so I don't see that as an issue in the future as an investor as it's baked into the town's business model and not likely to change.

After many problems over the last couple years, I really want to just let the situation take its course and get a new business owner in there.

My wife and I drive through there occasionally going to Pittsburgh and we've noticed a lot of new businesses to catch the new activity. 

To move someone out because they are having a hard time does not make good business sense, unless, you have the proper information.