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Crazy?
As long as we are on the old geezer kick, here is another one. And I have lived the corp life, not a life of physical activity. However, I make up for it by having 35 years of sailing experience, from dingy''s to offshore single-handing.
The biggest advice I would offer is to get out there on the water. It is more important to get actual experience than to sit there watching your stock portfolio (I know because I have been doing the same thing recently). Chartering is helpful. Racing in PHFR or local cruising races is extremely helpful. I did a bunch of local racing in the 60''s & 70''s and it taught me a ton about sail trim, weather, currents and navigation, with more intensity than just cruising or daysailing. It didn''t help much on learning boat systems, but it was very useful nonetheless. Deliveries are great--I''ve done quite a few--mostly crew--and learned from each one.
Owning your own boat and just taking it out each Sunday afternoon in decent weather is not particularly useful (I hear people screaming at this comment). All that does is keeping repeating the same lessons. You need variety of boats, crewing for a variety of skippers. I learned as much from the less competant skippers than from the best ones. Nothing like seeing bad judgement in action to learn what not to do and the consequences of mistakes.
Personally, I would not be too quick to buy anything larger than a daysailor for the next year or two. After you have sailed, say, a half dozen different cruising boats, then consider what you want. Many folks have talked about the boat size. My current boat is a 43, but I would not advise it for a novice--its fine for us, but the forces get much higher than a smaller boat and the consequences of a mistake are greater.
I did a bunch of single handing and racing on a Yankee 30 years ago, and if I had contemplated single-handed long term cruising then, it would have been a great boat for me.
The last item shows my own personal bias. The one thing that is not adjustable is time. Sure you can sail into your 60''s or later (e.g. Hiscocks et al). But you and I have more runway behind us than in front. So consider the value of this time. The Pardey''s said (paraphrase): Go small, Go now. I have friends in the midwest who have spent half their lives talking about cruising on a sailboat, but have not taken the steps to actually get out there. So go do it!!!
And I''ll see you out there.
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