most important/useful piece of advice I've ever gotten regarding boat selection: in the end, you'll sail what you got. which isn't particularly inspiring or definitive, but it helps me remember that the sailor is more important than the boat. If the thing is in good condition, and has a price you are comfortable with, you can't go wrong.
Sailing > Thinking about sailing
... or I'm wrong.
Living aboard, currently in the Chesapeake
O'Day 37, still new to us