FWIW... some of the crew for our upcoming Oct trip used Cheapoair to book through SJU (JetBlue) to Beef Island (Seaborne). On the arriving trip they have 2 hours 15 minutes between flights. They will have to disembark the JetBlue flight, go to baggage claim to get their bags, and then check in for the Seaborne flight. It seems doable but it could be tight.

I haven't booked yet so I'm not sure which way I'll go.