So, I am actually considering buying a nice cruising boat, 43-45 ft....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. ... Am I nuts?
You're not nuts, but you may be focusing on the wrong questions. Sailing is not the hard part of large-boat ownership, it's all the other things that make it challenging. Costs, logistics, maintenance, storage... You've got to learn to be a diesel mechanic, marine electrician, plumber, fibreglasser, rigger, marine sewer, propane technician, etc... IMO these
are the major challenges.
And if you are going to cruise long distances/times, then there are a whole whack of additional skills needed: anchoring, power management, long-distance communications, dingy choices, food/water/waste management, long-term stocking & storage, cooking, maintenance in remote areas...
Not trying to dissuade you at all. My first boat was a 34-footer. But in my experience sailing is the easiest part of sailboat ownership. Hire a skipper if that makes you more comfortable, but spend time with actual cruisers. That will help more than sailing with a skipper.