What are some US cities that meet my climate preferences for at least half the year?

So I realize that most people asking about an ideal climate are looking for something year-round, however, I’m in a pretty nomadic, travel-motivated part of my life at the moment and I’m not necessarily looking to spend more than 6 to 9 Months in a particular place (mostly in the interest of saving up money for future travels and to not have a constant gap on my résumé). Basically, I don’t need to pay top dollar to live somewhere that’s pleasant year-round given that I don’t necessarily expect to settle down right now.

So, climate: my ideal range (in Fahrenheit) is low 50s to low 70s, but with the most important factor being my intense dislike of full-on sun and cloudless skies. I don’t mind a little bit of sun if there’s a good amount of cloud cover, though similarly, I don’t at all mind overcast skies as long as the sun pops out for a couple hours at least once or twice a week.

And because I’m not totally impractical, I don’t mind going slightly outside that range if it’s no more than a couple months or so (and because I don’t typically work outside jobs, so i wont mind mostly staying indoors for a couple months). On the lower end of that range, I can go down to 25-35 if there’s not much wind chill, however on the upper end I can really only go up to 80-85 (preferably not much humidity, but I also know that drier climates tend to have cloudless skies more often that not, so I’m willing to go somewhere in the middle).

Lastly, I mostly work jobs in social services, so I’d need a mid-sized city at the very least.

Oh, one more thing — I don’t necessarily need great public transit if I’m living in an area with good access to hiking in the mountains (because I’d want a car for the hiking access), but if it’s somewhere without much hiking access OR a city that’s so busy that owning and driving a car would be a point of stress, then decent transit is necessary :)

Everything else is negotiable. Anything that fits my needs? Thanks!