I largely concur with a lot of the problems folks have brought up with your plan, but I won't repeat them. Here's another out-of-the-box suggestion for you:
Sell everything you want to sell. If you like risk, put some of it in the stock market and see what happens. Take some time off to travel to disney or wherever else with family/friends. Backpack, bike, hike, whatever, and aggressively pursue opportunities to crew on boats, and especially on deliveries. Deliveries will often be off-season, rushed, and to weather
and therefore much less pleasant, but the crew will often be experienced and the boat equipment
much more tested. You'll learn tons and get the experience you need to pick a boat
you'll be happy with for however long you decide to cruise
, and the experience to set a realistic schedule, decide about Bear, etc. Do this for a year or more. You may find, as many do, that the cruising life isn't for you, or as some of us do that you want to do it for way more than 3 years. Somewhere along the way, in fact, you'll probably run into the perfect boat in the not so perfect place, selling for a song because the owner is done or has suffered a family
misfortune. You can buy it and take off in your travels from there and eventually end up somewhere where boat prices are higher (e.g., USA or Europe) and maybe even do better than break even when you're ready to sell (something that's not too easy to do with boats.) Experience is your friend and you're young. Don't hurry, "hire the expert" first, and become one.