That sounds like a lot of packing and unpacking and time wasted traveling. There is also the logistics to consider, and cost. Ferries to Anegada only run three days/week, plus a Sunday morning run. Getting from Anegada to Jost would involve a ferry to Road Town, taxi to West End and ferry to Jost. You don't say when you want to do this trip, but Cane Garden Bay is overrun with cruise ship people, although less so in very low season.
Have you looked at options? Maybe chartering a smaller monohull. Another option would be staying on Virgin Gorda, doing Dive BVI's day trip to Jost and a day trip by ferry to Anegada. Look at Guavaberry Spring Bay. Look at renting a house on Great Camanoe that comes with a boat to do day trips.
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