I do not have experience with above ground but I believe that would be fine if done tastefully. 

Learn of course, but many of us have purchased properties throughout our career without "iron clad" veils and have done just fine.  

That kind of restriction just doesn’t work for someone like me.I’m trying to figure out if I might be missing something in how I’m approaching this or if others have insights or examples of towns that not only allow STRs but also have laws that offer enough flexibility to operate in the way I’m aiming for.Many towns technically permit STRs but impose restrictive rules like membership requirements, ownership duration limits, or rental day caps, making operations challenging.

I was fine with all these numbers.Then I met with contractors...First, I wanted to add a new bathroom and approximately 450 sq ft of additional living space.

Closing in an entity is fine on a DSCR loan. 

They might be fine managing new construction, but I have seem MANY investors almost tank from their fee schedule on managing older homes...i would compare it to almost predatory practice.

I like to look for board orders, excessive fines for weeds/grass, stop orders, and unsecured premises. 

Tenant took photos and videos but nothing detailed - a single shot or two of a room from the entrance, so is saying fridge was fine, normal wear etc Next - If we are being nice and deducting ‘portions’ of the charges and tenant continues to grind away, or this goes to court, do the compromise and smaller amounts offered negate the full amounts that could have been charged

If I can pay it off in a 7 years I’m fine.

Fine.