Shopped for about six months before buying. Saw a lot of tired boats with high asking prices. I think the market is different now - it's a buyers market at the moment.
Bought a Florida boat and had it trucked to Chicago. Not very expensive in 1990. Spent one season getting the boat ready and sailing on the Great Lakes to get used to it.
Went from a Sabre 34 to a Nordic 44. It was a big jump in size and took a little getting used to. Only 10 feet but 2-1/2 times the weight.
It also needed a lot of changes for cruising. Electric windlass, radar, wiring upgrade, new ham radio, new roller furling and forestay and a lot of other things I don't remember 20 years later.
Sailed through four of the five Great Lakes and Erie Canal to get to the ocean.