Compare that to when the driveway was put in.3) If your driveway has been there for at least 14 years, you can try to establish ownership via adverse possession law.

Consider converting one property into an STR while retaining the others as LTRs to establish a stable income base, taking into account your willingness to manage STR responsibilities, local regulations, and financial projections for each property scenario.

He doesn't buy liens in FL, but he does in other states.That says a lot to me.

Its a lot to take in  and I understand there are learning curves.

Back to your original topic (we investors do chase rabbits sometimes)...I am not aware of such a place that is not already in an established tourism/STR market.

If you can find some common ground, continue building on that to establish rapport.

The sooner you start the better. 1)look at other markets. 2) once you’ve established what you need, go see a couple of mortgage brokers and discuss your situation. 3)take action - buy something sooner rather than later. good luck, if you have questions, I’m happy to help. 

What is the best financing option for someone just getting in to real estate to purchase their first property and what does that process look like for someone just establishing a business?

I would say it's best to establish a long term relationship with who you prefer working with/someone who can service your needs now and in the future.

Due Diligence, background checks, deal reviews, the right paperwork, there's a lot to it.I started making a checklist of everything I check/verify before doing a loan, but I stopped when I had 3 pages, and I was still going.I'm not clear if you had a Note, a JV or some combination of both, but clearly, they did not value you as a lender.