Trying to Find the Ideal Anchorage!!

[Macopa]

I'm looking for a good anchorage with the following characteristics:
1. Safe/protected
2. Access to cell towers so I can get on the Internet
3. Isn't insanely expensive (1:1 USA or close)
4. Might be somewhere I can get a legit short-term job (bar tending, hospitality, business sector, etc.) English & Spanish good... Obviously clearing regs are an issue as well as visas...

Can anyone recommend such a place? I'm also looking for someplace that has surf although I'm sure almost anyplace in the Carib holds better than the Gulf Coast of FL San Juan, PR came to mind but I don't know about the crowds... Barbados has the surf but I don't know about the anchorages... Bahamas interests me and Eleuthera has surf but I don't know about working... Soooooo many variables.