We have used Fly BVI multiple times and they have been very accommodating and I continue to recommend them. Talk to Steve there if you can. (If you want to send me your name by PM I can put in a good word for you to Steve regarding your situation). Sometimes he will offer a discount in the slower months. I also checked with Dolphin and found them to be the same price as air charter. Air is so much nicer if you can afford it. Land in STT, they take you right over after getting your bags and you fly right over to Tortola Beef. We are always the only ones in line for customs and fly right through which is the biggest benefit other than timing.

I am pretty sure the departure tax is $20 per person regardless of where you leave from. Airport tax for leaving is an additional $20. If one charter is charging you less then they must be eating that cost into their price somehow from what I know of that process.

There are good docks at Cooper and Anegada if you want to go with those spots. Anegada is a long way for 5 days but if you like sailing a couple of hours a day, like me, then I would go assuming good weather. Sounds like you already know your limitations for days and places you like and I love that you are taking your Dad despite his disabilities. My Dad is 76 and had a blast when we took him last year. We had some minor difficulties but made it work.

I have not heard of VI connection but would definitely check into that further if cheaper and private. They had changed the rules the last I checked regarding where water taxis could drop you off. If they are allowed to drop you off at your charter company's dock after clearing customs like they used to, then that is a definite time saver and worth the money as well in my mind. At Dolphin's price, you are better off flying.