Depending on your sail schedule and how long you plan on spending will determine what your best point of entry will be.
In general entering from
PR is a marginal choice if your plan is to sail the USVI and BVI almost any time of the year. It is not typically a wonderful trip from SVI's to BVI's being against both the wind and seas, often on the nose.
If your spending a few months, that would change the story and allow you to select your sail dates depending on conditions. If you are considering a typical Charter of under 2 weeks, you may find the first half of your trip more difficult than most anticipate.
It is far easier to sail the BVI about any time. Pops over to St. John are rather simple and generally no problem at all and take just a few hours at most. To St. Thomas is only another short distance to the Red Hook area but the main harbor is several hours more distant but your going down wind and generally with the seas. Tons of really great places to visit in BVI and many interesting places on St. John and a nice anchorage on St. James is also fun. Most places on St. Thomas are .... well not so much fun for one reason or another. SVI is different and well worth the time IF you have lots of time or do not mind missing out on many of the "Must See" locations the other locations have.
You also have far more companies to choose from in USVI and even a much larger number and generally cheaper in the BVI.
I typically hang in the BVI / St John area but often have to make the run to the Airport on St Thomas and it is always a days WORK sailing or motor/sailing back to real cruising grounds that are enjoyable. When ever possible I have my guest come into West End Tortola or to Trellis Bay on Beef Island next to the Airport that services Tortola.
If your hard over on doing the
PR/ SVI's I would not recommend attempting to do must past St. Thomas unless you have more than two weeks cruising, but you would be missing most of the prime locations that make up this wonderful cruising area.