Catalina, Beneteau, or What ?
John, I''d like to offer you a somewhat different opinion than Jeff on selecting a boat. First, you seem very vague about the intended use of the boat. But more importantly, you may not appreciate the significance of caring for a larger boat, which will tend to be systems-intensive and which will be costly each and every time you add something to the boat.
OTOH I think you might be the ideal candidate for buying a newer smaller boat. New boats may require some upfront decisions about equipping but that also provides a useful learning curve for you. For a run of the mill boat, you won''t be making exotic choices. Moreover, you would have a warranty period, a dealer (assuming you shop wisely) and a manufacturer to support you, initially. Plus warranty periods on all the pricey pieces.
Perhaps I''m biased in this regard but after some small boat sailing and some formal instruction on a 34'' cruising boat, our first boat was a new 27'' sloop - basic but well equipped and very safe for offshore use (which was our only option, since we sailed out of Santa Barbara, CA). It was a great choice, initial problems were not JUST ours, and it was big enough to allow many hundreds of miles of ocean-coastal sailing while small enough to be manageable, affordable and comfortable.
Too many Americans want to own boats that are w-a-y too big for their needs. You don''t need to consider being another one...
Good luck on the fun!