The seed was planted there on that lake. But it took tell the time that I had established myself in a career before I could take on the challenge. A boat takes an investment of time, money and energy. You can of course substitute money for the other two. That is if you have an unending supply of money. Fiberglass doesn't eliminate the work involved but only changes its nature. Because of this I started at a sailing club on the Columbia river where I got the use of sailboats without having to do any maintenance. This might be ideal for many people. But after two sailing seasons at the club I decided that ownership was an important part of my dream.

After deciding to buy a boat I had find just the right one. New or Used? Well with my financial limitations new was out of the question. Under 25 feet would have been doable, but I wanted something with living space below decks. It had to be less than 30 feet because of the doubling of the prices for boats over 29 feet. There's also another jump in prices above 39 feet. For me 29 feet felt like the sweet spot. Boats this size are large enough to be reasonably comfortable down below and yet still small enough that I would be comfortable taking out by myself.
A number of people asked me about my boat ownership history when I was out looking at boats. They questioned my buying such a large boat for my first boat. All those who asked this question had gone the conventional route of starting under 25 ft and working their way up to a larger boat every couple of years. But I knew that I had only one shot at this. I would only be able to afford one yacht, and so I need to choose one that I would not grow out of in a couple of years hence. I had talked to the owner of Schooner Creek Boatworks at the boat show who told me to go over and look at the Cal 20's after I told him that the custom 36ft sailboat he was showing at the boatshow was way out of my price range. I did look and consider the Cal 20, but it was one of those boats that was intended on getting me on the ladder of boat ownership with buying a bigger boat in a few years.
There are not a whole lot of boats built in the 29 foot size. Boat builders seem to stay away from those size boundaries - Why build 29 footer when just a little bit larger and they can sale for twice as much. There was one boat builder operating under the philosophy of boat ownership where you bought the biggest boat you thought you would ever need, and pay for it in sweat equity. They sold most of their boats as a bare hull that the owners had to turn into a sailboat themselves. This was really not part of my plans. I had wanted a boat which would not take a lot of work to make serviceable, but there are few boats like this. The ones that are lovingly cared for, and are the pride and joy of an owner, so that they are unwilling to part with lightly. There were a couple of boat that I missed out on buying because the owners were unwilling to sell at a fair market price.
In the end I bought a thirty year old rundown Cascade 29 at a fair price. Not really a good price but an honest price. I thought I needed a boat that would take me any where in the world that I might ever choose to go. It still remains to be seen if this was a good criteria for choosing a boat. I spent a whole lot of time and effort to make the boat extremely robust, and now is capable of taking me across oceans.