advice on buying a cruising boat
I first learned to sail on a 15 foot boat MANY years ago. My first purchased boat was a 32 foot winged keel. Before I purchased this boat I spent about two weeks learning to handle a 38 foot full keel boat. After three years of practice, I bought a 40 foot Caliber. There is a world of difference in these boats. The 32 handles like a sports car - the 38 had a mind of her own - the 40 "listens" to me and while not as responsive as the 32 does what I tell her to :-)
My advice is to start in 30 foot range and then move up after you''ve "been there - done that" for a couple of years.