If I'm in your shoes (which I was a few years ago) I would recommend attending at least 1-2 real estate meetups a month to start putting yourself out there and networking with other players in your market. 

Otherwise, bite the bullet and pay the real players in this area for what they provide (Buildium, Appfolio, RentManager, etc).

Once you befriend one of these big players, ask who they use.

I hear a lot about standard personal loans, mortgages, etc - but do banks or smaller players consider situations like the above?

I can at minimum, provide insight into certain markets/ball players to connect with based on your strategy. 

Curious how you all would think a resort + casino going into a STR market will go and the impact?

Vacasa and Evolve are two of the major players that could have an opportunity in that area for you to be boots on the ground.

@Scott Trench Had a deal close last month with a combination of your scenarios/players.

Hes one of the bigger " players" in Ft Myers, also owns ( I assume still does) Social, top " clubs/ restaurants there.

Quote from @Gash Nookala: David has the right idea about building a team, but the most important player on that team is the property manager.