Join Date: Jan 2011
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It sounds like you're way ahead of the game. Take sailing lessons if you can. That's best, but if you can't, buy the boat and get out there. Instruction from books and Youtube will get you started and a string of "learning moments" on the water will teach you the reason why some things work and others don't. You probably have a good head on your shoulders, and you probably aren't a Yahoo. You'll do fine.
As far as the boat, consider something a little bit larger. My lovely bride and I bought a Lancer 25 four years ago. 25 foot is about as big a trailerable as you want to get. We tow her and launch her every time we sail. She takes about 1/2 hour to step and rig. The big benefit is room. If you'll be spending time on the water, space is a premium. Also head room and "head" room. Smaller boat ofter require crawling or squatting to get into and the head is often a porta-potti set in the middle of the cabin. And you also need room for a thing I like to call "Merlot Time". Even after 31 years of marriage, it's still important.
If I may be bold, pick up a copy of The Complete Trailer Sailor by Brian Gilbert (or something like it). In the back if the book he has a section on boats from 15 feet to 28 feet with photos, sketches, specs, pros and cons. It could help you pick the perfect boat for you.