Ok let m start by saying I live aboard a 44 yr old sail boat, so I may be a bit biased on this subject .
First things first Price ... the old saying goes that the happiest day in a boat owners life are the day of purchase and the day of sale , Now with the economy the way it is at the moment smaller vessels are in the reach of the common man but the 30 foot range and longer is starting at 100k dollars .
Now who has that kinda cash to drop on a say catalina or beneatu .
Used vessels may not come with all the bells and whistles of a brand new boat ( or the new boat smell ) but the have a character and a history about them , some of them may have done crossings or been around the great loop , some have rode out hurricanes or seen weather that would make a salty old dog like me run for the nearest harbor.
I have been in the marine industry a long time and have seen the "cruising" sailboat go from a working mans escape to the rich mans toy and I don't like it .
My old girl has seen 6000 + nautical miles under her keel and she still sails like she has somewhere to go, I guess what I am saying is buy an older boat fix her up and keep her floating and she will thank you .