In the early 70's I delivered boats to/from the Caribbean/New England Area. Never did the Thorny Patch (you ought to read Bruce Van Sant - Gentleman's Guide to Passages South and Tricks of the Trades) and only went via Bermuda or via Norfolk to Morehead City and then outside.
I would second (or third) the idea of the Caribbean 1500 for the first run south - as BillyR says, you will get at least 1 blow - you may spend a good bit of time with a reef and hard on the wind. Bermuda is a great 1/2 way point but it is 1/expensive and 2/a bit of a weather magnet. I'd do the Bahamas on the way north and enjoy the ride.
You've got time and I'm sure will have fun planning and thinking it through.
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