@Justin Ceballos thanks for the great advice, ive traveled for most of the island but honestly the only time im in the north is when i land in san juan.For the most part i stay in the southern part of the island from cabo rojo to humacao.

The owner is out of town and he got burned by the third party (they took off with rent, records, etc.) he tried using as management.

I think ach works best for both parties so getting low cost ach makes sense.i went with apartments.com then got a tenant who wants to pay cash and only communicates via text. 

Quote from @Chris Seveney: @Mackenzie MaeI have no clue who either party is- but if one party throws shade at the other they have a right to defend and let people also know if it’s been settledWhat private information did he put in the post?

Lastly I'd say research the demographic of the parties that partake in tourism in the area.

Some companies will only handle bits and pieces of the STR, so you could have one property management company and another company who is responsible for the maintenance and a third who is responsible for the cleaning and preparation of the property for the next guests.

If he does that he will have more than enough leads coming his way.It's also important to understand that he doesn't plan to manage for 3rd party clients long term. 

If something isn't working and one of the parties wants to move along, they should be free to do so unfettered.  

What you put out of a way for parties to transaction to wrap transaction cost's into financing, is EXACTLY how we got to today's system.

The harder part is enforcing violations.