We visit Trinidad every few years. My in-laws live in POS, in a gated community. If your employer is putting you up, you will most likely be living in one of these communities, with other expats. Schools are good, athough it doesn't sound like it would be a concern to you, education is very important to Trinidadians.
I am often warned about crime, kidnappings, etc., but I have never felt unsafe. I don't wander at night or go to crowded clubs or back alleys, though. The taxis do make me a bit nervous! lol
There is a lot to see in Trinidad and Tobago. I was just saying to hubby it has been way too long since we visited Asa Wright bird sanctuary. A trip by ferry to Tobago is also in order!
The beaches in Trinidad are usually a long, harrowing drive but well worth it, and once you have a "Bake and Shark", you will never want to leave!
The complex where my in-laws live is on the ocean, but not a swimmable area, but provides great views and a wonderful breeze to keep you cool. There is also a pool where they provide swimming lessons for the children. There is a great two-level shopping mall nearby and a good grocery store. Yes, selection on goods is less than in the US/Canada, but still quite liveable. If you needed a housekeeper or nanny, your company would most likely be able to provide those things for you, too.
The lifestyle there, like most islands, is very laid-back, so if you are supervising locally-hired workers, you may become frustrated with the pace at which they move, but they are for the most part a friendly, reliable, genuine people.
I cannot wait to go back!