Yeah but then I'm just out $20k? At least buying a boat gives me some equity that I can later recoup even if it's at a loss.
Having recently purchased an Alberg 30 myself, with the same kind of goal in mind, I've got a few thoughts on that.
The costs of a boat are truly staggering. While I'm enjoying the learning, and the idea of it being MY boat still appeals, the quantities of money involved even for a small cheap boat blow me away. It requires a total readjustment of the expenses involved in something, at least for me. I've never in my life budgeted for things in the thousands of dollars the way a boat requires. If I'd known just how drastic that difference was, I doubt I would have bought a boat, though I'm glad I didn't know in some ways.
Would you prefer to spend 10, 000$ for a fantastic adventure, with great equipment, and a safe roomy boat, or spend 20k up front, a lot more in getting your boat sorted out, and be lucky to only lose 10-15, 000$ at the end assuming you did the work yourself and didn't get any surprises?
A tangible asset is only good if you are getting back more than you would have spent to rent. Otherwise it's just an expensive liability.
I was budgeting a year or two for learning to sail properly, as well as living on her at anchor to get used to the conditions I might be experiencing later.
I've done the learn as you go thing with a motorcycle, and though I enjoyed it, I don't care to repeat the experience with a boat.
Learning things the hard way gets less appealing as the close calls add up, especially with someone else's life in the mix.
I would think that you could have a fantastic adventure for 10, 000$, and that would be with a safe, roomy, well equipped boat, and supplies etc being provided.
In hindsight, I would have preferred to have started that way, but I too balked at the cost, I felt I would be better served buying the boat, and selling again later. I paid 10, 000$ for my Alberg 30 in the end, though with a year of moorage so I can refit her, and sorting out the electrical system I've already passed 20k$, with no sign of slowing down any time soon. I haven't even started the interior refit, adding tank capacity, safety equipment, training, spare parts, tools, electronics. I never wanted a project, but that is the reality of older boats.
I'm reminded of a joke about farming, paraphrased for sailboats the best way to get 10, 000$ with a sailboat is to start with 30, 000$.
I'll be quite pleased, and a bit surprised if I only lose 10, 000$.