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Hey Midnite,
You don't give too many details, so it's hard to know exactly how to advise you.
You say that you are waiting until your girlfriend's son graduates from HS. So, I'm going to assume that schools aren't going to be an issue for you to consider.
I don't know if you are retired, or if you will still have to work. Obviously, Jax would probably offer a lot more employment opportunities, but on the other hand St. Augustine could be great if you are retired or employed in the tourism and service industries.
All things being equal, I would recommend St. Augustine. What a great little town. Great beaches, great history, a surprising number of good restaurants considering it's size, and a nice laid back artsy atmosphere. I can't say enough good things about SA.
If you have trouble choosing between JAX and SA, you might want to consider Ponte Vedra Beach or Vilano Beach, two nice communities located between Jax and St. Augustine.
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