So, I am actually considering buying a nice cruising boat, 43-45 ft.
However, my wife and I don't have much experience, we sail a small Hunter 19 now and have trained on a 33. We both don't want to go through the slow size growth over the next 10 years to work our way up. We know what we want in terms of size and comfort for us and the family. Do people ever just jump in and buy a good sized boat and hire skippers to work with them until they are comfortable? We realize we need additional skills, training, experience etc.., but I'd love to get moving faster since we are coming to the game at age 50.
Where would one find a qualified skipper to work with? Am I nuts?
You are not nuts. However, 10 years is a long time. You can plan for death and taxes but everything else is just a craps shoot.
What do you want to do now? What are your plans for next summer? You don't have to go through multiple bouts of 2footitis but you can buy a boat now and another in 10 years.
If weekending and vacation length coastal cruising type boating is what you have in mind for the next few years then I would maybe get something that you are comfortable with.
Since you didn't mention budget or geographic location that makes it a harder to answer.
A family of four could comfortably weekend/2 week cruise on a modern 33 ft boat. If you are in say New England or the Chesapeake Bay area you could spend a lifetime and maybe not hit every little port town within 12 hours sail.
That 33 footer is something you could also easily day sail and single hand.