I try to avoid SWA, but we have flown SWA out of Hobby before to SJU. There is only one non-stop on Saturday which gets in too late. The flight you mentioned departs Hobby at 5:25 am with a plane change in Orlando before arriving SJU at 1:25 pm. It's a long day, and travel time for us to Hobby is much more difficult than to Intercontinental.
Our last two years in Barths, we have missed our return flight back due to Tradewind issues....GMP62 was on our flight two years ago. Last year we attempted a landing in SJU during a rain storm, missed the runway, circled a bit, and then the co-pilot told us we were low on fuel and would have to go to St. Thomas. Once we landed STT, everyone and every piece of luggage had to get off the plane to clear customs. What a hassle.
This year we are going to check out of our villa late, have a boozy lunch at Pearl Beach before heading to San Juan. Overnight and then catch the 7:00 am flight to Houston on United.