Athens, GA gets a B- from me.
Pros
- Winters are cool enough not to have to use air conditioning
- Plenty of steady, soaking rain events during the winter, with occasional wintry precipitation
- Spring weather arrives in March instead of April
- Somewhat lower tornado risk than the rest of the deep South
- An extra month of summer weather
- Fall is mostly sunny and dry with warm days and cool nights
- Typically enough chill in the air by sunset around Christmastime to get people in the holiday spirit
Cons
- Not enough wintry precipitation
- Too cold to do much outdoors during the winter despite a relative lack of wintry precipitation
- Severe weather season starts earlier than most places
- Occasional high-pressure "wedges" result in cool, gloomy weather during the spring
- Very humid and prone to triple-digit heat during the summer
- The relentless heat and humidity gets old by August
- A secondary severe weather season during the late fall
- Occasional warm spells in December create a Christmas buzzkill
By the way, I lived in Pittsburgh for 15 years, and it's actually not perpetually cloudy there. The cloud cover is most persistent from November through March. That's when it can be excessive. It's actually quite pleasant from June through October. (April and May are variable.) Here's a picture I took in September 2010:
And here's a picture somebody on the Pittsburgh forum took in June 2012:
If a typical Pittsburgh summer was relentlessly cloudy or rainy, then PNC Park would have been built with a retractable roof to compensate for it. Pittsburgh is cloudier than the average city in the United States, but the United States is sunnier than most of Europe and Asia, so it's all relative anyway.