Pros & cons for your climate by season

Winter
Pros:
Nothing.
Cons:
- The cold
- Snow; it's bad to have to walk in when they haven't plowed the sidewalks, and annoying to clear off your car when you drive somewhere as well.
- The sunny days tend to be the coldest days. "Oh it must be nice out; it's sunny!" "The high was 2 F today!"
- It drags on past the official end date of the season too.
- Having to put on extra clothing to keep "warm" (it's still a farce)
- Fewer people are available to socialize because nobody wants to go out in the shitty weather
- Did I mention it's cold as hell?

Spring
Pros:
- The best potential for upward temperature variation; we've had 80s in March before
- The snow melts; yay!
- It's beautiful when leaves finally pop out on trees
- No more depressing 7:30+ AM sunrises
Cons:
- The cold isn't over yet; we've had huge snowstorms in April and 30s highs in May before
- Mud, slop, puddles, etc. as the snow melts. Yuck.
- March can probably join November as the blandest month, just 30s-40s and cloudy most days

Summer
Pros:
- The big one: it's mild to warm most days, great for outdoor recreation
- Usually a decent amount of decent thunderstorms
- Shorts and T-shirt weather at least 90% of the time
- More social events and people doing things around town, taking advantage of the warmth as it is fleeting
- Sunniest time of year, with many afternoons also featuring neat cumulus clouds
Cons:
- True heat is rare, fleeting when it does occur, and usually coupled with intense humidity
- Temps are at their most stable, so we can get stuck in an infinite loop of 81/63 and partly cloudy
- Sometimes the storms have a talent for avoiding my area
- The glorious warmth can still be broken up by highs in the 50s-60s and lows in the 40s, even in July

Autumn
Pros:
- Foliage can be beautiful in mid to late October
- There's some seasonal lag, so September is still nice and mild, and October usually still has quite a few nice days in the 60s and 70s
- An Indian summer where it's in the mid-70s in early November (or 80s in mid-late October) with low dew points, early sunsets, and half-bare trees is the most surreal, and epic, feature of our climate when it occurs
- While not as known for storms as spring and summer, there can still be surprisingly decent activity as late as November
Cons:
- Almost 8 AM sunrises right before we fall back
- You know any last bit of mildness after mid-October is fleeting so you feel bad if it's a weekday and you can't enjoy it as much as you'd like
- October snow can happen, e.g. white Halloween of 2019 (but then brown Christmas)
- The way things look in Nov/Dec (as well as March and April). Everything is gray or brown and looks dead.