Notably, we were able to work with local lawmakers to adjust a proposed bill that would've included STR's in an "empty home tax" that would've essentially made all the STR's on the island unprofitable.

I think the Brandon Hall proposal is very interesting.

If you are just getting started, good insurance may be the better play.Assuming you have a large portfolio, you know how to manage an LLC properly, are willing to take on the added paperwork and expense, and are not piercing the corporate veil by having mortgages in your name, here are my reactions to your proposals. 

If they are $600 below market, and market is $1200 you are proposing doubling their rent.  

In the H.R. 3936, Built in America Act, it was proposed to extend the 100% bonus depreciation until January 1, 2027.

There's nothing specifically wrong with your proposal, but I'd just do a rate and term conventional refi and forget the LLC.

This can lead to a more productive conversation and help you refine your proposal

If the terms they are proposing seem good to be true, they most likely are. 

@Shayan Sameer, like Marc notes, confirm funding of HOA and proposed or pending special assessments.  

Make sure your lender is on board with the purchase price and DTI ratio you are proposing.