I think that many boats are registered to LLCs, that shouldn't be cause for worry. I've cleared in at Road Town when coming from St. Martin before and it is particularly inconvenient, there is no dinghy dock for you to use. You could clear in on JVD, and if asked state that when you were going between Prickly Pear and Neckar you realized it was too early for Spanish Town and that you just continued on to JVD since that was your destination. I used to use Gun Creek to clear in, but I am given to understand that they are not open yet (after Irma).

The downhill run from St. Martin is a lot better than working upwind from the BVI, but you will have the wind and waves almost right behind you so it will be a rolly ride. I often end up tacking downwind to minimize roll and that adds a lot of miles to the passage.