You're asking the right questions. While I hesitate to claim expertice in any particular area, I'm in year number 5 of a very similar plan to yours; cold start to sailing away. At present I have about two years to earliest possible sail-away date (751 days, to be exact). So here are some thoughts in hindsight:
already touched on it. You've defined a goal, (I assume the wife is on board) now build a roadmap. Money will define the boat you ultimately buy, when, where, and what training you get, how long you can cruise and what you come back to, etc... Finances are every bit as important as learning seamanship.
-Training: Three aspects: 1) Self directed learning: Read and watch everything you can. Study where your interest takes you. My first book was Sailing for Dummies. 2) Formal training: To bareboat charter most places (that is charter a cruising boat without hiring a skipper) you will need to complete ASA 104 or the US Sailing equivelent. Sailing classes are extemely helpful but as many here will point out; the time the school devotes to the curriculum is inadequate which brings up the third aspect, Experience: Even the oldtimers here (especially the oldtimers) will tell you they learn something every time they go out. So go sailing every chance you get! Charter boat, friend's boat, your boat, skipper or crew... it doesn't matter, just get sailing. Start a log and record your sailing days and some notes about the experience. (I use a simple excel spreadsheet). Good judgement comes from experience, experience comes from bad judgement.
-A boat: Boats are expensive, so is chartering. Chartering the costs are all up front. Owning, you get to experience "care and feeding." Buying a ready-to-sail boat is usually much less costly than buying a fixer-upper. However, nothing will teach you about boat systems like repairing boat systems. You need some experience to know what you want in a boat (performance characteristics and amenenities). Consider a small boat to learn the basics, then upgrade when the time is right.