Pros: Amazing coffee. When the weather is great, it's great. Everyone rides bikes.
Cons: When the weather is terrible, it rains every day for a month. Everyone rides bikes.

Portland is recognized by most everyone as the premier bicycle city in America, or at the very least in the top three. There is tons of bicycle infrastructure and advocacy, no shortage of shops, and seemingly everyone rides one kind of bike or another. Constant periods of rain put a literal damper on things, but the mild winters should more than make up for a need for fenders in the spring. If you're the type to spend more on your bike than your car, Portland is calling.