Everyone's experience is different. We've done three round trips through SJU in the past year without issue. Because we were using Cape Air coupons, we had to pick up and recheck our bags. They don't have luggage carts, so we used a porter. One connecting flight was on Silver. No issue there either.

My one trip on the Bomba Charger from St. Thomas, years ago, cured me of that route. It broke down a dozen times, spewing diesel fumes, which caused a baby to barf all over Ratman. They ended the run in West End, and we got to pay for a cab to Trellis Bay.

Some of our neighbors charter a plane from St. Thomas, which is a good option, if you have enough people to split the cost.