Fever !
About the "bigger boat" fever that Joe is suffering from...
One little suggestion, if I may, is to look at boat sizes in terms of displacement and sailing repute, and finally LOA.
I have limited experience in boat buying, but have always kept in mind a statement by NA Bob Perry. I may not have all the exect words in proper order, but the gist of it is to:
Decide how much *minimum* interior you actually need to make you happy; then buy all the waterline length you can afford; finally, it should always make you smile when you row away from it and look back.
As I recall the general context, from several decades ago, he was not advising a spartan existance, but rather cautioning about buying too much interior that you do not need. Of course, DWL is the *one* feature that gives you the most speed under sail or power. That and avoiding excessive beam-to-length ratios.
Which reminds me of some other advice from yacht designer Ted Brewer -- look for boats where the outside was designed first, i.e. for sailing, and then a cruising interior was fitted into that shape. He laments that so many "modern" sailboats are designed the other way around.
As to my opening thought, when we were shopping, we decided to focus on the amount of boat (displacement) that we were comparing, one to another.
That observation helped lead us to our Olson 34, which displaces about the same as a beamy Catalina 30.... and is light years faster. Both are about 10'10" in beam, but for comparison, our design rates 99 (!) down in SF Bay.
You should not particularly want a boat just like mine... but do consider the viewpoints of sailor/designers like Brewer and Perry. Along with Bruce King, Tom Wylie, and Raymond Richards, I consider these guys "royalty" in the world of sail boat designs for people who intend to leave the dock and actually go sailing.
Opinions rendered on the hour, deposit .03 (price raised due to $$ devaluation)
Loren