Great advice with all of the comments and I have a couple more data points to add.

First CYOA are great folks. We chartered with them a few times and I think they are good people with a great location.

A couple of years ago we bought our own boat and we keep it at Sapphire Beach in the winter so we make the trek to the BVI's several times every season. Since we are on the east side of the island it is an easy reach right up to Jost and as others have said that is a great place to check in.

Having said that I will say that recently, Jost has gotten a bit more tense than in times past. For example I checked in 3 weeks ago and I was quizzed several times if we are a private vessel. They were looking at the passenger list and saw a different last name for two of our passengers. When I explained that the two people were my wife's parents and that "trust me they don't pay to be on the boat" obviously meant as a joke but he didn't crack a smile. Ok maybe my timing is off but usually I can get them to lighten and smile. Not really the case recently.

Next example is from Christmas week (again at Jost) when I got asked a few times as to how much food I had on board. Puzzled, I asked him what he meant and he asked how much was the food worth? I explained that we had between $100 and $200 worth of food and he finally accepted that as an answer.

Now I want to be very clear. I think checking in and out of the BVI and the USVI is still very easy and should not be a concern to people. I have always been treated well and the folks seem to want to do their jobs well on both sides of the borders. It is a tough job and I think we as travelers should slow down and be empathetic to what they deal with on a daily basis.

If you are going to go in and out a couple of times a season ask to buy their forms. it is like a dime for the personal immigration form and 50 cents for the boat form. It allows you to fill the forms out on board and take you time.

Capt Jay if you are reading this you should provide these forms to your customers it would be a cheap but really nice touch. Same with the US forms that are free. Show your customers how to fill them out so that the "mystery" is debunked.

Last thought (I promise). When coming back to the US it seems to be getting easier most of the time. However, just like the BVI there are inconsistencies. Sometimes I am asked about any garbage on board coming in from the BVI. I have always subscribed to confess up front. If I have a bag of trash I bring it with me and if asked I tell them I have it. They then have an agent look at the bag ask questions and dispose of it for us. I do try not to come back in with trash but sometimes cant help. The other one that happened recently was that in November I was charged a $6.66 fee for entering the US but the last three times since then I wasn't charged at all. Not sure why but I think what it tells me is there are inconsistencies no matter the country. What has always worked for me is to be candid relaxed and honest. The rest seems to work out.

Enjoy your trip.