The first sailboat was a Catalina 27. Learned to sail on it, sailed around Chesapeake Bay for 5 years, then decided I needed something larger.
After lots of research, driving more than 5,000 miles looking at them, I found a 33 Morgan Out Island. It's big enough to live on, lots and lots of room, sails extremely well, and easily single handed. Morgan stopped making these boats many years ago, and finding one in decent shape was somewhat difficult, but I eventually found one just 50 miles from home in Rock Hall, MD.
Good luck on your search,