Originally Posted by Dockhead
... Learn to sail really well in dinghies, then buy whatever boat you plan to spend years on, and can afford, and spend the "starter boat" period getting it into good condition and set up the way you like it. This process takes years and $$$$$$$$.
I take the opposite tack, I always encourage people to postpone buying
a boat in favor of building experience, but they rarely listen to me!
I think an advantage of sailing lots of other boats is gaining knowledge and learning what you like before you buy.
It helps to broaden your experience too if you can sail lots of boats in lots of different venues & conditions.
You can do this by crewing
in races, joining a sailing club, chartering, crewing on deliveries...
Of course it also depends on where you foresee your sailing future going. If you just want to cruise
your own boat then maybe experience on lots of other boats is less important (though I think its still valuable). I wandered down the path of sailing instructor...charter captain
...cruiser...so the experience on a lot of different boats served me well.
Something I really enjoy about sailing other people's boats now as a charter
or delivery captain
is that I can hand them my maintenance list at the end of the run and walk away! Can't do that on a boat you own...you get a lot more sailing time in, versus maintenance time & $'s, on boats you don't own.
Learning on other peoples boats still takes years, but a lot fewer $'s.