I spent a few years in a club that offered lessons to it's members at half price (US Sailing) and chartered boats at half off too. It ended up being cheaper than owning for that period and the instruction was top notch. That way you can get instruction and time on the water without a lot of cash outlay. The club I was at had a variety of boats, so you could try out different ones and get a better feel for what you like and don't like before you go and buy.
Anyway, I was a moderately experienced small boat sailor with very little larger boat experience and I found the classes invaluable even though most of the 'book' material was a review.
When I was ready to buy I left the club knowing a lot more about what I wanted.
That particular club had a program where you could buy one of their boats as long as you kept it it in the club for a couple of years, earning a percentage on it's rental, no slip fee, and they did the maintenance. If I had lived closer I might have thought about it.
(windworks in seattle