Yes, that is the question. One might ask why I am here, posting on a forum for people involved with sailboats when I've only been sailing a half dozen times, and currently don't even own a boat, much less a sail.
Sailing is one of those things that I've wanted to really get into since I was young... my first time was in 6th grade, some 40-odd years ago. My dad almost got a sailboat when I was a teen, but couldn't work a deal, and ended up with a power boat. I took sailing lessons quite a bit later, and almost ended up with a small sailboat myself one time. But something always ended up getting in the way... a job change, a move that precluded boating, or family issues.
Now however, the kids are getting older, and I'm getting closer to retirement, and I'm thinking about that sailboat again. Not the little one... the big one. Oh, its still a few years off... but I've figured its time to start working in that direction.
I've always enjoyed building things, and I've convinced myself that I can build a boat too. Of course, one doesn't just jump into such things (or at least, I don't). I figure this will be a three step process.
First, I plan to build a small sailing dinghy. I've already selected some plans (Glen-L "Eight Ball"), which I expect to complete over the winter. Not that I really need a dinghy, but I figure its a relatively inexpensive way to see if I really want to build a boat.
Assuming that it turns out I like boat building, I plan to move on to an over-nighter in the 20 foot range, which is as large as will fit in my garage (the back yard not being much larger, nor level, and the HOA not favoring outside projects). This will easily fit on a trailer, and will allow me to visit local lakes, while still having enough heft to handle coastal sailing.
I figure this will have to keep me busy until I can retire, sometime in the next 8 - 15 years. That is the point I figure that I can relocate closer the the Atlantic, and find room to build my dream boat. I am thinking something big enough to live aboard part time, or do some serious cruising. My current thoughts lead me to believe that 40-45 feet is the right range for me and my wife. However, I've got several years to think about this, and I'm sure that these forums will provide me plenty of information to base any decision on.