Kyoto is worth multiple visits. Tokyo too, but for quite different reasons. (Kyoto is beauty and history. Tokyo is…a universe in itself.)
I love Melbourne and Munich but feel no need to re-visit Sydney or Salzburg.
Pervert.
mmm
We enjoyed Madrid; lots of good tapas bars and nice plazas. It’s easy to get to scenic places like Toledo from there.
I’ve been to New Orleans multiple times and every time I’m there I discover something new that I love about the city. Will be going back forever.
My limited experience:
Multiple visits- Washington (so many museums), Chicago, Detroit (my own bias), Toronto, San Francisco, Orlando
Once is plenty- Denver, New Orleans, Rapid City, Phoenix (too damn hot)
No desire to ever visit: Miami, Branson, Nashville, Houston
I don’t get the love for New Orleans. So they don’t have many restrictions on alcohol. Sure, you can get great food and music, but you’ve just about got to beat the panhandlers off with a stick. “I can tell you what city you got your shoes, what street you got your shoes…”
Great food, great music and great culture will always overshadow panhandlers. I don’t really see how lots of panhandlers would keep me away from a city that has so much else to offer.
Those who are just giving Kansas City a single day - how big of a role are you giving food as one of the reasons to visit in the first place? I’m partial to KC because I grew up there - but even now I’m trying to find new BBQ places, or other fun restaurants to try when I go back.
I’ll give Louisville a “more than once” vote for those who might be interested in the Bourbon Trail. In addition to that, there’s plenty else to do downtown, though I wouldn’t stay more than 2 days.
I could spend a week in DC and not get bored.
Cleveland is worth going to at least once. True connoisseurs of the culinary and fine arts will see it fit for multiple visits 
Madison, Wisconsin?? I live here and I love it, but there is nothing here at all for tourists, really, unless it’s scoping out hot co-eds. And there’s hanging out on the Union Terrace with a cold beer and listening to local bands – a nice thing to do, but still …
In terms of big cities (ones most people have heard of) my total list is Indianapolis. Now if we’re talking small cities that would be a much larger list. I love places like Tipton Indiana, Winchester Virginia and all of Lake George New York as examples.