I'm considering RV slots ( for Snowbirds, vacationers, and refinery/turnaround workers), MH pads, cabins, etc. 

You're trying to book vacationers via Calendly?

@Justin R.Marco Island is a top destination for vacationers.

Obviously I want the property to be in a nice section so I can attract decent tenants (vacationers).

Yes, there is a lot of competition for vacationers.

I live 2 hours out of the city, so having my own property to book and stay in would provide a huge personal benefit in terms of being able to head into the city more without the stress or hotel fees.I guess I'm mostly hoping to hear if anyone has done this ... my initial concerns are (1) potential complexities with how the entity is set up/ business or otherwise/managing the books, (2) negative perception among vacationers in a complex or duplex format, and (3) finding a property manager that can manage some of the nuance of STR (such as cleanings) with the general maintenance of LTR.

You may do better buying, fixing up and then renting out the homes to vacationers... but I would check into that too.

The tax meant to pass on to vacationers.

@Marci SteinIsn't Sullivan county full of orthodox Jewish summer vacationers, what towns have the rentals for the winter months?

 -1 Bed Rent: $500/month-2 Bed Rent: $600/month-C Class apartment building which we are doing a value add too.My Concerns:-C Class apartment building-Don't want the Vacationers to have a bad stay and then leave bad reviews on AirBnB Host account for future investments.