Re: My Rough plan to get better at sailing.
I think it's a great plan.
But...I still think you should just buy a boat. A cheaper one. I think you'll lean more quicker.
Is maintenance a pain in the ass? Of course, but how are ou going to learn about boat maintenance if you're not forced to do it. If its your boat you'll care more,
You'll try to make thinks last, you'll come up with new ways to fix things. That's how you learn so when you are circumnavigating and something ones wrong you will know what to do.
If you buy a good boat for not too much your costs can be less than the cost of the yearly membership. It may sound great right now when it's 80 an sunny every day but what are going to do in winter? Use it once every two months? Why do you think they require the yearly membership?
If you have your own boat you can learn to anchor, you can take a weekend trip to the San Juan's, a couple weeks in October to Canada. Spend a weekend at bell harbor paying $25 a night to be sleeping right out in front of pike place market. Store your foul weather gear there, sleep at the marina just to get out of the house. Smell your boat that smells like you, make it your own. Save some money and buy you first GPS. Get a good one so when you upgrade boats you'll still have it. Start a library of PNW cruising an anchor out in the south sound and dream about the places you'll cruise next year. Worry if its ok whe a winter storm comes and go down to the harbor at three in the morning to snug your dock lines.
Throw yourself into the fire. You'll learn more than you think.