When I settled into the Little Pueblo in southern New Mexico, a reader wanted to know how I selected it as my "retirement town." The short answer is outdoor lifestyle, climate, and altitude. But I like polemics like this, so let's look at the longer answer.
Perhaps my opinions on this topic are of limited use to couples who care about how much house they can afford in any given area. I'm done with the house thing.
The basic decision is whether you want to look at a city as a grown-up or as an eyelash-fluttering Romanticist. The Romanticist is turned on by extremes: for instance they might choose a "vibrant" city that gets a lot of positive publicity, such as Portland OR. It's not exciting and romantic to consider the traffic, the anthill busyness, and the high cost of living in a big city.
The Romanticist could just as easily flip to the other extreme by pining for a "quaint and charming" hamlet, while yawning about its lack of a doctor, good grocery store, civic organizations, etc., unless Bible church, bowling, watching high school sports, and satellite television is your dream lifestyle.
The Romanticist might be turned on by world class scenery nearby, completely overlooking how quickly the "scenery effect" wears off. It's best to compare scenery with odor regarding its effects on a person. The world is set up so that places that have spectacular scenery have little of anything else. To choose a retirement town based on scenery shows that you are still thinking like a vacationing tourist. There are exceptions: St. George UT has world class scenery and is large enough for other amenities, such as LDS churches and triple digit heat all summer.
The Romanticist might dream of a perfect, undiscovered, dream town in the mountains or on the beach. Undiscovered? Get serious.
People who have a large retirement budget can consider places that others must reject, such as Prescott AZ. But if I had the budget to live there I would choose to do something more interesting, such as travel the world.
Perhaps the most successful commercial formula for a retirement dream is the McMansion next to a golf course. Such developments probably use design-software that lays the development out to have the maximum number of McMansions bordering the golf course. From the air the convoluted fairways look like green intestines. The houses, sticking to the edges, look like polyps.
And yet, ironically, it could be argued that a romantic approach to retirement is the most practical of all, since it opposes the ennui of old age. Without some kind of dream, what would the oldster do but cocoon? Frankly, if the couch-potato lifestyle is your future, what difference does it make where you "live." (As long as costs are low and there are plenty of doctors nearby.)
With regards to a retirement town, a long-time RV traveler like me is probably incapable of romanticizing a place for more than the 14 days. But I can dream about a way of life.