Back when I was first sailboat shopping I knew nothing about them. Sure, I picked up a few books, but it always helps to talk to someone with more experience. So there's this guy I knew who was rebuilding a small sailboat in Maine. In fact I talked to this guy on the phone the day I decided to pick up my Oday 19.
I thought it'd be great to go spend a few days sailing together once his boat was finished. That day has yet to come as his boat is still being rebuilt. He is paying an awful lot of attention to detail. I'm more of a “good enough now let's get in the water” sort of guy.
Recently I built a boat in my driveway. It took a couple of summers working off and on -more off than on. It took long enough and it was only a 12 foot boat. Once a boat gets over 20 feet, building it yourself isn't very economical. There are plenty of good used boats out there for small money. If you want to get out on the water for little money, buy used instead of building.
However, some people aren't really into sailing. What they are into is building a boat. If you are one of those people, go right ahead and build a boat. There are worse hobbies. I get it, having built a few small boats myself.
I can't help but look at boat designs and think how I could build the perfect shallow draft coastal cruiser. Something like Dave Z's most recent boat
comes to mind. His boat is being built to fit his very individualistic needs and he's doing it using pretty basic materials and tools. Using a lot of ordinary lumber yard materials, it's a pretty cheap build, but still more expensive than buying a used boat.
One thing about Dave's boat, it will be in the water in a reasonable amount of time. Too often I see boat projects outliving the builder. Even if they actually complete the boat, they are sometimes too old to sail it anywhere.
Fiberglass changed everything. Mass production using semi-skilled labor turned out a lot of boats. They last a very long time, much longer than most people expected. Fiberglass is repairable. I once had drinks on a very nice sailing catamaran that the guy picked up for very little. It was beautiful and I could not believe the price. He took me down below and showed me where one of the hulls had been nearly cut in two in a collision. That was the state he bought it in. In six months he rebuilt the boat to where it was impossible to see the damage from the outside. He left the inside in a rougher condition as it didn't hurt the function of the boat and was normally hidden by a fabric liner.
If you want to do boat work, save a ton of money, and go out on the water in a reasonable time frame, picking up a fixer upper boat is the way to go. However, if what you really want to do is to go now, there are plenty of used boats in nearly sail away condition.
You've got to ask yourself: are you a boat user or a boat builder? Or, what sort of blend of builder/sailer are you?