USMC, after many years of powerboating and restoring my own old wooden boats while I was in the USN (enlisted guy trying to restore a wooden 40-footer on an E-6
budget none-the-less!) I decided to try sailing although I had never sailed before. Bought a book, read it thoroughly many times over, and bought a 21-foot O'Day with a 9-HP Yamaha
outboard for $1200 and then the day comes to actually go to the marina where the boat sat (James River near Norfolk, Va.). Luckily the boat was small and light enough that I could push off the 2 or 3 much larger (and more expensive) boats that I nearly bumped into pulling out of the marina because I didn't know anything about sailboats. Once in the open
water of the river, I handled the
sails so badly that I was surprised that I sailed the 12-miles to where my powerboat was docked (private dock). Over the ensuing months I talked with a lot of the "old salts" and watched the sailboats from the local
sailing school while sitting at
anchor and learned a lot. The following year I thought that I had to have a bigger boat so purchased a
Catalina 27....was never comfortable on that boat for more than 3-days. The boat sailed great! But the
interior layout just didn't do anything for me. Have recently purchased an older
Hunter 27 as a
liveaboard (It's just me and it's much larger than crew quarters on a US
Navy ship!).
You mentioned the you have time, 10-years I believe you said. Take your time and listen to everyone on here (Except me...I'm a complete
novice when compared to the likes of Ann and Jim, Stumble, RKO, and many others) when they tell you to take some lessons, learn the theory, learn to
repair the technical systems on a boat, learn
fiberglass and
gelcoat repair, learn what you want/need on your boat, play on other people's boat, keep your partner fully involved at all times and go have fun. Good Luck!