My first boat, Flying Lady, was a good introduction to sailing; but I decided that I wanted to look into upgrading - maybe something a little nicer and perhaps larger. Our one family vacation on her had proven her to be inadequate for a family of 4 even though she "supposedly" slept 5 people.
I began to do as much research as I could especially on the internet. Early on in my sailing career I had found the Trailer Sailor Bulletin Board forum and the members are great for bouncing ideas around and getting advice. The board represents a vast array of boating and sailing experience and they proved very helpful. I also visited several owner forums paying particular attention to owner reviews. I even took a couple days and went to the coastal areas of NC to visit some marinas and look at several particular boats up close and personal. I looked at a Macgregor 25 in Elizabeth City and a San Juan 24 in New Bern - not boats for sale but they were on my list of possibilities. I visited the Rhodes plant in Edenton and looked at the Rhodes 22 - a very nice boat, well thought out but even used boats were pricey. I saw a Compac 23 in Oriental - a boat I really like but it weighs a little more than my car would pull. The SJ 24 had a great interior but was really about the same issue - weight.
After much deliberation I settled on a Macgregor 26C. The water ballast made the boat much lighter to trailer, no fixed keel made her easy to launch and retrieve, the interior included a queen size berth, after some initial tenderness she stiffens up nicely, and she was reportedly a quick and fast boat. All of this and they were also affordable. So the search to find one for sale began. I found one in West Milford, NJ on Greenwood Lake. The owners were in their 80's and were giving up sailing. They had bought the boat new and had kept her on the Hudson River in the summers. After some negotiating I bought the 1990 model for $5600. That was in 2004.
I christened her Heaven Bound. As many boat names have double meanings, so would ours. Sailing off into the sunset can indeed be heavenly; and as Christians, we are heaven bound when we leave this life.
I sold her in 2012 for $5500. She was actually worth more than that but the gunnel on the starboard side had gotten crunched against the piling at my pier when the fenders slipped out of position. My home repair was pretty good but still it was there. The motor also had a problem with cutting out when you put it in reverse. Turned out that was a minor fix. Oh, well. Still not bad for 8 years of enjoyment.
Oh, yea - the new owner is a Christian too and loves the name. You can read about the new adventures of s/v Heaven Bound here.