[camaraderie]

Chuckie...I wouldn''t head out much before November 1 as you can still get hurricanes and big storms forming even past 11/1.
I guess I am puzzled by your rush to get south especially if you are buying a new boat.
1. With a new boat you want to be able to test and upgrade all systems necessary and make sure she runs well in offshore conditions. The place to do that is in the States where parts and repairs can be made quickly and efficiently. A run down the ICW and maybe a couple of easy offshore hops would do this for you...but a "buy in Florida and depart" plan would not. If you do buy in FL, suggest you take a trip down the keys (using the Hawk Channel)and back before you leave the country. This will take you a week to 10 days depending on weather and how hard you push. Again...wait till November to do this.
2. Once you are ready to jump offshore, the trip down the "thorny path" you noted can take as little as 3 weeks but is more likely to take a couple of months due to the easting you have to make against prevailing winds and waves that simply won''t let you travel for weeks at a time. For example...we had to hole up in the DR for a full month last year to get a 3 day weather window to make it to Puerto Rico...and had to stop for more than a week in other spots along the way as well. If your question about making it by Christmas is to accomodate visits from friends or family...I would tell you to forget it...you can''t let deadlines impact your cruising safety and it is a tough enough trip in the best of weather.
3. Why not enjoy the trip rather than press for distance. You can spend months in the Abacos and Exumas in water and beauty that EXCEEDS anything I''ve found in the Carribean while being close to home and having a helpful and large cruising community nearby.
From there, you can do the offshore route to the Virgins in a week to 10 days or go the thorny path in a coupe of months but at least haveing had some time to decompress and get your boat and living aboard style sorted out before making a tough slog to weather for 700+ miles.
Sorry to run on so long, but yell back if you have questions on anything else. BTW...read Bruce VanSants Guide to Passages South if you don''t already have it.