[camaraderie]

There are lots of boats available for sale in both the Virgin Islands and in Trinidad...many of them blue water capable. English is the language in Trinidad so no worries about Venezuela. There ARE problems in buying a boat in both places in that there are "hurricane" boats which have been structurally damaged and repaired...but sometimes not so well AND charter boats which have been hard grounded and may have hidden problems.
This is complicated by a very small surveyor community that may not have your best interests at heart. My suggestion would be that if you find a boat in the islands, that you MUST have an extensive boat AND engine survey by a surveyor you KNOW you can trust based on other friends recommendations OR one that you fly in from the States despite the expense.

As to doing the trip from the states...it is hard and can take 90 days or more island hopping from Florida and waiting for the trade winds/weather to moderate so you can make progress to windward. You must have a solid and reliable vessel that is well prepared for this trip as there are long stretches where NO boat services are available and you must have the parts and skill to handle breakdowns.....not something you would want to do on a "new to you" boat that has yet to be tested.
Another alternative if you buy a boat in the USA...is to cruise the Bahamas 700 islands and the East Coast and the Florida Keys and then head off to Bermuda and the Azores and Europe when complete. The Bahamas are a paradise once you are outside of Nassau!
Suggest you search yachtworld.com advanced search for available choices by geography.
Good luck and let us know how it goes!