Minimum Skills to Bootstrap into Cruising
I have thought of a million ways to ask this question, but basically: How do I jump feet first into a cruising lifestyle without "drowning" in the process? What are the minimum skills (not just sailing, but repair, cooking, "life" skills, etc) needed to get started, and what else will I just pick up along the way?
I am a single young guy (mid 20's) and I really want to get out there cruising ASAP. I've taken some US Sail courses, done some charters, and own a small boat I practice on at the lake. I felt confident and ready, enough that I almost put an offer in on a boat (a BEAUTIFUL and well price 27' Orion) but quickly decided I need a little more time, if nothing else to shore up my Cruising Kitty.
When I do buy a boat I plan to take at least a season or two to get to know the boat, make upgrades, get used to repairing it and so on. But in almost making that offer I realized how huge the gulf was between what I know and what I feel I need to know to get started. Like repairing mechanical systems... I've never tinkered with a Diesel Engine before. Or fiberglass repair and maintenance... until I got my little boat last year I knew nothing, and am still rather clueless. And on and on.
I need to keep my job (3 hours from the coast) so I can save more money. If I keep my job I really can't crew on other people's cruises (no time) or gain experience that way. I don't feel I have enough experience to buy a big boat, But if I don't get a boat I wont have a "sandbox" to learn things. So I'm saving money, but not building up needed skills... AGHHHH
I read as much as I can, but book knowledge only takes you so far!
So when I get the money should I just say "screw it" and jump in? Or are there a list of a few key skills that you just HAVE to have (aside from how to sail and navigate) before you can safely start cruising? And how do you get those skills while still stuck as a landlubber?