A surprisingly unscientific answer for a scientist, albeit a brony one.
Conducting a survey of people -> subjective results
Using the same formula on every city -> standardized objective climate score result
As meteorologists, all I'm asking for are metrics that can be used to build said formula (and even suggest a formula if you're up to it). Yes, the creation of that formula is subjective, but that doesn't concern me because as long as that same formula is used across all the data, then all the resulting climate scores will be relative to each other and you can compare them. Which would be pretty cool.
I'll start: perhaps ClimateScore = AverageAnnualLowTemp + Average(AverageAnnualHighTemp,AverageAnnualHighTemp), and then some other operation involving humidity, or perhaps rainfall. Or even % cloudy/sunny days in a given year.
See? It can be a fun problem to think about.