I have been at ZSU for about year, so I can't really comment on working the traffic. Lots of non-radar and foreign facility coordination. The facility has been great though. I showed up at the same time as almost 20 other people, so training got backed up, but we go to D1 pay pretty quick (a couple months). the whole "every day is a training day" seems to be fairly well accepted, although there are controllers at every facility who want nothing to do with training.
Our ATM (Boston John Melecio) seems,at least from what I can see, to really be a "Controller's manager".
San Juan itself is... well, at the risk of offending any puerto ricans, its a dump. its all concrete and potholes. but drive 25-30 minutes away from the airport and the island is beautiful. Driving can get interesting. red lights and stop signs, lane markings, right of way laws, those are all just suggestions here. people here are incredibly nice people, until they get behind a steering wheel.
The language barrier isn't really a big deal here. I only speak a little spanish, and while I get a lot of "you live in PR now, you need to learn spanish!" most people know at least a little english, or there is someone nearby who does. government services seem to be the one exception.
Im happy to answer any other questions anyone might have.