The biggest issue with doing this imo is twofold..... give yourself plenty of time/time cushion, and have plenty of cash so you can be flexible.
Time, if the weather just isn't nice, don't force anything. The problem is, if you reserve anything, you're under a deadline to get there by X and mother nature might say she has other ideas. The only way around this would be to book for the earliest time you want to be there, or any place to and from, and pay for more days upfront in case you're delayed. You want to stay 7 days, book places for 10. you want 10 days, book for 2 weeks. Irks me that something would be sitting there empty waiting on me to get there, but I would rather have it than have nothing.
Which means - Cash! lol imo, this is easily a 8k-10k trip.
Obviously a plumbed in fuel fill source, epirb, back up gps-es, and two vf's would be bare minimum. And I was informed the is no way this happens unless I put Bruce's refridge mod on the boat lol
our hoped for plan ideally would be to make chub day one, and northern beginning of exumas by day two, then take 2 days getting to Staniel. Stay in staniel at least 7 days, one or 2 days back up to nassau/chub, then spend 2 days in bimini possibly. so 14 days minimum.
As said earlier, my wife (iffy if she would boat the whole way) would meet us in nassau with my son (no way he makes the crossing, nassau to exuma chain would be an omg for him and hes a water monkey - just the thought for both of them of being out of sight of land is a major hurdle) My daughter is like me, dreaming of this and completely in!