Many Caribbean hotel/resorts and restaurants are closed in October so you'll have to check if the ones people recommend will, in fact, be open. the good thing is at that time of year room rates are at their lowest so your $6,000 budget will go far.

That said, for condos check out some of the many "condo-resorts" on Grace Bay on the island of Providenciales in the Turks & Caicos. There are at least 20 different "resorts" you can choose from.

St. Martin has quite a few "time share" condos that are available for rent. It's one of the more "year round" populated islands so you'll find fewer closures. No need for going AI on this islands as it has hundreds of restaurants, beach bars and roadside stands where you can dine fairly reasonably.

If you are intent on going AI look at resorts in the Dominican Republic - it's the AI capital of the Caribbean. You'll also find lots of AI's in Cancun and Playa del Carmen.

Thanks we will definitely make sure the resorts we look at are, in fact, open. Most I've seen still take customers but at a discounted rate because, as you said, it's low season. We are also looking for places in Central America or Mexico since there is less risk of hurricane weather there. I'll be sure to check out the types of places you suggested though.