In '96 I went back & forth from Fort Lauderdale
to the Bahamas
4 times (8 crossings). There are boats that have been there for years "Waiting for weather".
Granted, it can be rough if you get wind
but the fact is, it doesn't happen very often.
Talk to some of the guys that make frequent trips. Some of the locals sail over there once a month. If there are no cold fronts.....just go. It's like a 6-8 hour sail and you need to be mindful of your drift. There are cruising guides
that will tell you exactly how & when. Just don't get hung up on "Perfect". Perfect seldom happens and OK is good enough.