Having completed this specific route via Southwest 3 times in the last year, we’ve had plenty of time. Granted, this is with carry on only,
Assuming you land on time, no need for VIP service.
The time to walk from arrival gate to exit the airport’s secure area, which you’ll have to do through baggage claim, takes about 5 minutes.
Passing through the exit system will require your ID and Tradewind connecting flight info and/or the Puerto Rico completed entry form. Clarification that it’s not required if you’re in transit (have done both) but you leave the secured area, exit the building, turn left, continue straight to elevators, go up to departures, go to terminal 1 (used to be A) and go to Tradewind desk. Sounds complicated, it isn’t.