We only uploaded our letter from Cigna saying our medical insurance covered us worldwide. We have MedJet, but didn't include that (would have, had they asked).

The tricky bit is the quarantine. If your PCR test is positive, you won't be able to fly to Puerto Rico, and getting retested for a false positive isn't immediate. You might be able to ferry to the USVI if you had that advance test.

Or you could be stuck in the BVI, paying for a hotel for two weeks. It has happened. We own our house, so that may be why they didn't care.