Welcome to the forum and don't worry about asking questions. I think I can say with a high degree of certainty that few, if any of us, were born expert sailors. Pretty much everyone here had to start out as a newbie at some point in time.
In general you will find that no questions are considered dumb questions. The only place I see some lack of patience in replies on the forum are when the asker has obviously done no basic research
prior to asking some very basic question.
So, you have the right idea already. Research this forum and the internet
in general as very many of the new sailor questions have been addressed in great detail. Also, helps to do some basic self education so get books
and read, read, read.
Regarding the USVI, have not been there for many years, but have not heard of any blanket restrictions against liveaboards. Some of the moorings may be owned by charter
companies so may be restricted in that regard. Also, I would usually prefer to use and trust my own anchor than a mooring
anyway. Just because you see an available mooring ball floating in a harbor does not mean that it is safe and ready to use.
Also, there are plenty of places besides the USVI that I would recommend. The VI is a convenient place for air connections, supplies, etc but after a while starts looking crowded and touristy.