Here’s my experience. First, our boat is registered with home land security and has the necessary annual sticker (number on sticker) is needed with the ROAM apt. You don’t need to check out of the USVI.
Regarding checking back into the BVI. When we check out of the BVI, I have filled out a form that names the boat AND ALL the people on board. This form has multiple copies. We keep 3 copies and then return them when we return. We do fill out the individual small forms for each person but I don’t know what happens if there’s a change of names on that form. Bear in mind when we check out of the BVI onboard our cat for a short visit to St Johns we don’t pay the required $20 per person departing fee because we are all listed as returning and then pay that fee when we finally leave on a ferry. I’d be very clear about your intentions with BVI customs when you leave just so you have no surprises when you return. They can be a pain if they want to be especially if things are out of the ordinary. We always check back in at West End and check out at Great Harbor.