I have a mix of long term rentals and STRs and rent some of my STSs mid term in the off season so I am happy to share my thoughts and experiences with each strategy in this area.  

Pensacola has a lot of potential, and I’ve seen investors do really well in the area with both long-term and short-term rentals.Since you’re just getting started, here are a few tips that might help:Know Your Market: Pensacola’s mix of military families, college students, and tourists means there’s a steady demand for rentals.

Quote from @John Warren: @Mordechai Chaimovitz cap rates and NOI are commercial real estate terms, and 1-4 units are not really valued in the same way.

What are some key tips and websites that you know about that I can use in terms of RE Financing?

On the initial agreement, it clearly stated that the buyer was going to be using financing and listed the terms of their financing

On long-term rentals the bank likes to see signed leases which clearly you can't have with STR. 

The only investments I’d do there is in short-term rentals in either Rome, Venice or Florence.

They are all on separate parcels, paid off and occupied by long term tenants.

I think it would be better just to stay on good terms and let him know you will contact him when you are ready to sell.

This term replaced "subprime" and looks a lot different than subprime loans of the past.