@Traumagas You don't say how much experience you have. Time on the
water will teach you if you're able to make it through the challenging times so you can enjoy the delightful times.
Charter a boat of the type you'd like (doesn't have to be the same model) and take notes (You say "Type A" so you know how to take notes. ;-) regarding what you like and dislike. Do some charters in waters that might be somewhat (but not too) challenging. You'll soon learn if you're both up to it.
You don't say how good you are at self sufficiency and fixing things. Things break on boats and you have to be prepared to handle them. If you're not adept at fixing things, then chartering may be the best option. If you want to know what can go wrong on a
Leopard, look at our blog svlux.blogspot.com 2005 L40 and/or watch the YouTube channel "Gone with the Wynns" (200X L43).
We are not full time cruisers. We've done several long-ish trips to the
Bahamas and on the Atlantic
ICW. We come back to
family and friends. It's an alternative that works for us. The Commuter Cruiser is another alternative - cruising half time.
Finally, there are often two fears that counter each other:
* Fear of the commitment to leave.
* Fear of not taking the opportunity to leave.
Determine what you need to do to overcome the fear of leaving. What
safety net do you need and how much does it cost? This is why many posters say that you'll know when it's time.