Your list looks good but as others mentioned it doesn't hurt to think long term and explore refi options as well.

I would say if you do post it be as detailed as possible minus borrower info re: what's the collateral exactly (estimated value, condition, etc), outstanding balance, state where it's held, terms, performing or non, 1st or 2nd position, payment amount and what you're asking price wise.

Short term or long term?

As a business we run a note fund and also syndicate notes that we originate or purchase.  

Total rents at 100% occupancy across the three are $2900 monthly.I'm thinking because the financing terms are soooo attractive that it may be worth the higher risk that comes with the high PITI?

Sub 2 was not in my vocabulary 3 years ago when I started in Real Estate, now Sub 2 or buying subject to its existing financing is a common term I use daily!

This was in 2019 when I was funded so the terms were much more favorable than they are now.

You also need to talk about your terms.

I am planning to start a direct booking site for my short-term rentals.

Its going to be more about those factors than any local market factors for DSCR Lenders.The lender should have gone over the prepayment provisions more closely before closing, but assuming you likely have whats called a "stepdown" prepayment penalty shorthand called "5/4/3/2/1" - this means that you can refinance and prepay, however if done in the first year of term you will have to pay a 5% fee, second year 4%, third year 3% etc.