This topic gets some play every year around this time. Do a search on this site, and you will find plenty of info from this time last year. Sorry, but it's hardly an original idea.
Season in PR and the Caribbean runs Nov-April. You can probably find work, but you will have to go there and knock on doors. You won;t be looking for a "HR person", though, you will be looking for the Chief Pilot. You should also know that you are talking about a sweaty, dirty job, where you will probably be expected to load and unload your cargo, and a DC3 holds a lot- and it's all uphill.
For contact info, try
http://raa.org/members/AirlineDirectory.htm and see what info you can find there. Again, you will have to go there, they tend to hire locals or people with at least enough interest to actually got there and look around.
Good luck. Like I said, it can be done, but not by sitting on your can stateside, that's for sure. If you go, make sure to try Isla Grande airport, too, which is just outside old San Juan. Also Vieques/Culebra. You may want to try Fly BVI out of Tortola.