I live in Rincon, NW corner of PR. Last year, when it became apparent we'd maintain a place here, we decided to buy a car. Previously, in NJ, we only bought cars new, for cash. In PR we did not want to lay out all that cash so for the first time decided to buy a used car. We'd go out frequently to the used car places on the highway and this got to be pretty depressing. I also did some research (by asking around and looking around) and most cars are Japanese or Korean, on the small side. I narrowed down which car I wanted: a 2007 Toyota Yaris - it had great reviews. Forget about the used car dealers on the highway! The place to look is Classificados Online (on the internet). I quickly found out that good cars go fast after they are listed. So I started looking early in the morning and that worked - I was the first person to call about the car we have now, a 2007 Totota Yaris with 70,000 miles on it, they asked $8,000 I got it for $7,700 and love it!
If you want to ship a car from the States then you can expect to pay something like $4,000 in shipping costs and import taxes (most of it import taxes). Also determine if it will be easy to get your car serviced based on what car you are shipping.
If you will be making PR your permanent residence then you should evaluate your tax situation. Puerto rico has it's own tax codes, separate from the States. If all of your income is generated in PR then you will not have to file US Fed taxes. But you will have to pay Fed Social Security and Medicaid taxes, the same as if you were in the States. If you have some income generated in the States then you might have to file PR, Fed, and US state taxes. If you move to PR during the year then for that year you'll have to do taxes for PR, Fed and US State. You'll need to do some research, see an accountant, and even better, meet and talk to people in PR who have been through this.
Will you assimilate easily into PR? Depends. Your husband will be hanging out in a high end resort teaching golf. If you spend most of your time i n a high end enclave and spend most of your time with affluent expats then should be pretty easy. But I'll make a general statement: if you like hispanic culture then you'll do fine, if you don't then you might not. My wife and I have love living in Rincon, we like the culture, the sun, the ocean and the simple life. We live in a Puerto Rican neighborhood, we are the only North Americans. The culture here includes warmth and friendliness, relaxed environment, but also lots of noise, inefficient government service (got to allocate a at least one day to either register your car or get a driver's license), loss of electricity and water every so often. But then again you'll be living in a high end area.
Let me know if you have any questions. If you visit Rincon (it is a popular vacation place for people from San Juan) look us up, my email is victorlglass@gmail.com