Expedia - Multiple Airlines - Risky???
I think DJ Mom may have said it best---depends on whether you are a worrier. I am not, at least as to travel stuff, so take my advice with a grain of salt. Most times it works out, sometimes it doesn't---if you take this approach you need to roll with the punches. Weather is generally not a factor in February in the Caribbean, though planes can have mechanical issues at any time. For under $100 per ticket I might opt for a single connection---depends on the value of that money to you.
---Jim
So I did book the ticket. I travel pretty often for business and don't get too worked-up over "stuff". I did, however, book a later flight from San Juan into STT. We now have 2.5 hours on the ground in San Juan. If our US Airways flight is a little late - no worries. It it's on time - no worries either - I'm sure we can relax with a cocktail and get excited about the rest of the vacation. We now leave Lexington at 9:21am and get into San Juan at 4:14 (with over an hour layover in Charlotte). We don't leave San Juan until 6:55 and get to STT at 7:25pm.
Thanks again for all of the advice. I'll let you know how it went in my post-vacation trip report!
Thanks again for all of the advice. I'll let you know how it went in my post-vacation trip report!

Chances are you're probably going to be just fine with that amount of time in SJU. I'm not sure but you may have to change terminals in San Juan so you may have to go back through security but that's not a big deal in such a small airport. Hopefully your bag will have enough time to change from US Air to American's flight.