I don't have any suggestions on places to stay that aren't already mentioned. I'll just add that I'd make sure you carefully plan out the logistics going between places so you don't spend too much time dealing with going in between. As an example, ending on Jost might make sense if you can take a ferry back to STT from west end. I think Virgin Gorda would be out unless you started there, then Anegada followed by your last stay on Tortola?

If it was me, I'd figure out the ferry schedules and other travel related schedules and see which places offered us the most time in each location.

And I have to ask as my curiosity gets the better of me.. why a land trip vs boat given you want to visit multiple islands?