Hey Ace,
I could not recommend ownership more highly - if you can afford it, buy the 150 (after confirming it is in the condition you expect, and airworthy). I bought mine in 1987, and could not be happier that I did!
Not too long, I posted on a thread on this subject, it might be informative for you. The whole thread is here
http://www.pprune.org/private-flying...c150-pa28.html There is a wealth of help in keeping 150's in the air happily. A 150D is a good choice for a number of reasons.
Puerto Rico looks like a great place to fly around, as long as you don't bump into a cruise ship on short final into San Juan! It appeared that they stopped air traffic during our arrival and departure within the harbour...
As long as you take proper care of it, you'll not regret buying a 150. It will always be salable when you want to move on. Though, after 23 years, I've found mine so dependable and economical, I have never thought to move up.
Pilot DAR