Though not yet retired, our goal is to winter somewhere, so we built criteria that looked like this:
Warm - This rules out almost everywhere since we are only concerned about Jan-March temperatures. We also, for the moment, only want to look in the states.
College or University nearby - A great way to take in a play, see a good bar band, or watch a game.
Water - We disagree on this one. I think a great golf course pool suffices. My wife would like to see a big body of water.
Hockey - Yes. We're from Minnesota
Seasonal Golf Memberships OR excellent social golf program - I'm already a member of a course up here. I don't want to be a member of two courses, but I do want the socialization that membership provides.
Hiking and Biking (The hiking one really hurts southern Florida's intrigue for me)
Not super crowded - I have friends in Ft Myers that never venture from their communities because of the insane traffic.
Price - Though not a huge concern, it's still on the list.
I'm missing a bunch, as it's not in front of me, but with WARM and not crowded being really important to the list, we narrowed it down to about 10 cities. This year, we have an extended trip to Tucson. It matched every criteria except water. Though it's a hair colder than Phoenix, it bordered on acceptable. They even have hockey (going to 4 games in March)!
The point of my post is that Tucson is barely listed in any of those "where to retire" articles. The only reason why I even looked at the city was because it popped up on my hockey criteria.