I feel there's a bit of overkill here. You don't need to read Chapmans cover to cover but nice to have. Mine is a reference book, just like my Calder, Gerr and others. You don't need a capts license, don't need 30 years experience, don't need to be prepared for an electrical failure in a fog bank or other "multiple" emergencies..... just too rare. You don't need to be prepared for ALL possible things. Hire a captain for training, they should teach you enough basics to get you by and keep you safe. You should be able to dock a twin with a single engine only. Know how to handle basic emergencies and systems failures. It's not that hard.
Paul said to hire the "best" training captain... go down to Ft. Pierce and hire Capt. Chris, you won't go wrong. Go to Ft. Myers and charter a boat (with a training capt for a week or a few days, you'll learn a ton.
Peter said a smaller 40ish boat might be a better first choice. Agreed, both because it's easier to buy, operate, maintain and sell than a much larger one, and you can do a LOT of cruising on a 40' boat... even the Bahamas. Heck, look at Peter in his 36' Willard doing the California to Florida run.
And before you venture into open water and the Bahamas, you'll want to bone up on weather and forecasting. You can use Chris Parker for good wx info on your first few trips over there.
We all started out as beginners and some have advanced quite rapidly. We have loopers that have had rapid training and done well on the loop.
Yes, it's very doable, and you'll get a lot of good ideas here.