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re: First boat: Cal 2-27, Pearson 28 or Islander 28?
I think your analysis is a reasonable one. I started sailing high performance dingys, and still do. I also windsurf and sail my 30 ft keel boat. I really do think the learning curve is much faster in a dingy, but that does not mean you should go buy one. As long as you are conservative with your first sails, and perhaps take someone with you with more exerience, you should be fine. Your choice for a first sailboat is good, solid and safe if in good repair. I am surprised when inexperienced sailors buy a big new boat, it must be pretty depressing the first time you bounce it off the dock.
Thank you for the reassurance, it is good to know I'm not totally off my rocker
As for bigger boats, I was really tempted at first. Dreamed about crossing oceans and all that. But then, I've made that mistake before, when I tried to get into motorcycles. Bought a brand new 130hp sport bike... it's been sitting in the garage for the past 4 years with only 2000 miles on the clock. I remembered that when I was lusting over that beautiful Cal 3-30 or an Olson 30 add in Latitude. Bottom line, I still have a 5 year old daughter and a beautiful wife to home to, so I doubt I'll be taking stupid risks.
Having said that, a few hours in a dingy will teach you sail control and other skills that can take days to master on a bigger boat. Try to get out on a Laser or similar aboat at at local club. You will be glad you did.
Now that is a very good idea. I don't think I'll want to start that way, but will definitely give it a try if only to gain an appreciation for that type of sailing.