OK here's me, a relative newbie. Hubby and I sailed a day sailer (actually a racing boat, a Thistle) at barely controllable speeds during summers on a local lake, the past two years. We mostly avoided crash landings.
Last year we spent the entire season shopping for a bigger more comfortable boat (my minimum requirements were: a cabin and a head). We traveled around the northeast looking everywhere. He wanted a C&C for speed and I wanted a Catalina for easy sailing. Finally we settled on a Catalina 27 that was already at our local lake; no shipping expense or hassles needed.
So this year we are enjoying going out every day possible and I am actually sailing the boat myself. It's enormous fun!