Cruising isn't something you "do" it's something you "are." There's not really a getting-ready phase and then you're done and you don't do anything any more except sail and play. As long as you're on your boat, you're repairing and modifying and maintaining and improving. So, in the 4 years you have left: figure out how you're going to get your mail and pay your bills while traveling; whittle down your possessions; install in your boat the critical systems for safety and comfort and whatever makes you feel like you're not camping out. Sail a lot, anchor out on weekends to get those systems further refined. Move aboard before the 4 years are up, if that's practical - you learn a lot while living aboard even at the dock.
Then go! If necessary, you'll stay in some port for a while making modifications and upgrades, but you'll be having adventures!
Yes. As usual my friend WNW has it.
First, forget the term cruiser and remember the term 'mobile-live aboard'. That is what you have to start thinking. Sell the house and store the things you simply do not think you can sell. Just forget about that stuff for a while. Now, focus on being a live aboard. We all are. Some are just more mobile than others. Who cares? Get your boat early and start learning her. Don't wait until you are retired, then have the pension, then start selling the house, then start researching boats, etc. you will bee 900 years old before you get out. Instead, start your process now. It will take longer than you think. Enjoy living in a marina and learning. THEN start putting together the pieces so when your job is done, the only thing holding you back is dock lines. Sounds easy, but it isn't. You will be tied up another year before you are ready to go.
My point is to start the beginning of your life now. Btw, as I type this, I am anchored off Snead island, then Venice tomorrow, cabbage key next day, fort Myers beach, then tortugas for A week...
You could be here too.