I certainly haven't considered moving just to escape weather that is unpleasant for all or part of the year. I find that places that have year-round pleasant weather also tend to have some combination of a high cost of living or restricted opportunity to attain economic autonomy. (The two often go together.)
In terms of the car ownership experience, I live in Kansas about 200 miles from the triple point where climate zones Cfa, Dfa, and BSk come together, so I don't have to worry about underbody corrosion from deicing chemicals. However, the combination of heat and humidity in summer can be very unpleasant in wet years, and with an older car this is a more serious problem at the margin because it is harder to maintain an elderly R-134a air-conditioning system in good working order than it was with R-12. R-134a is a smaller molecule, so it leaks more easily; it is also a less effective refrigerant, so compressor output tends to become an issue after a couple of decades.
However, in terms of homeownership upper Cfa is better than lower Dfa because of reduced risk of rooftop ice damming from a period of prolonged snowfall. We have never had this problem here in Wichita, but up in Omaha (300 miles north) a few years ago it led to many homeowners dealing with roof leaks.
Littoral and montane geographies also introduce layers of problems additional to those brought by climate.
