Ryan, renting a place in PR to learn the market better sounds like a good idea.   

It would be a good idea to assess your tolerance to risk and then plan something like that, but using a heloc is going to be around 9-11% in this market so to pay something off with lower interest rate to borrow more might not make much sense.

Even if it's a total rehab if the land bank has a property in an area where the arv's are substantially high wouldn't that be a good deal or a promising neighborhood for buy and hold.

I know leaving a w-2 isn't an overnight change, but I love the idea of financial independence and would love to not be reliant on it.

Do I continue to hold it and hope the appreciation eventually makes for a more palatable return?

After they book, it's still a good idea to use the platform app for communication because then the platform has a record of what you and the guest have said, in case you need it when a guest does damage and admits it to you, but later denies it to the platform.  

Quote from @Mark Sullivan: Quote from @Jimmy Murray: @Mark Sullivan if you are a buy and hold investor these loans work great.

I do think partnering might be a good idea for you, especially if you're somewhat limited on capital.

Working with a private lender can indeed come with challenges, particularly regarding qualifications and funding structures.For your cosigner, they typically will need to be a member of your LLC and the private lender will want them to hold 51% - depending on lender of course.Compensating your cosigner fairly is based on what both parties believe is fair.

It's good that you have two ideas to start with.