Re: Cal 21 or Santana 22 for first time sailor
I think I would go for a swing keel boat. Which would be much easier to launch from a trailer. However, if you are looking at two specific boats, it will really come down to what condition each one is in. One of them might be a complete disaster.
Don't plan on crossing the lake on a small boat. I went from a Catalina 22 to a Bristol 27 in order to feel more confident on the lake. Stick with Manistee Lake, or harbor hop up the Michigan coast (Michigan ports are generally said to be nicer than Wisconsin anyway)