I'll second (or 22nd) the sentiments on MCO - worst airport for the frequent traveler I can think of.

I also agree that you can't compare major airports with small, regional airports.

If you are looking at large airports, I would nominate PIT. Having gone from MCO as a home airport to PIT, I now realize it's possible to have a set-up where all gates require a shuttle to get to without having to sprout a few more gray hairs each time you transit.

Further, what makes an airport hassle free....I'm currently in NOLA, and while MSY seems hassle-free, it also takes forever to get there from d/t. I think this is another benefit of some airports (SAN comes to mind).