I grew up in a boring town called Beaverton, which is just outside Portland, and I never really went into the city too much, just the occasional walk along the river or concert. I went to college for 5 years, and now I am living in Portland. I couldn't be happier.
I live in the Southwest area, right by Portland State University. I'm really starting to discover what makes this city so great, and what I was missing all of those years being just 20 minutes away.
The food. Portland is nationally known for having great food, but what sets it apart from other cities, is that our great food isn't in fancy restaurants and diners; it's everywhere. The small podunk bar, the burrito van; it's all really good. We have some damn good fancy restaurants too. =)
The bars. We have a lot of bars, and many of them have great music. My current favorite is called the Candlelight, a small jazz bar that has live music every night at 9pm. Pool table and friendly folks too. There's another, Kelly's Olympia I believe is the name. Vintage motorcycles hang from the ceiling, and I always have an amazing time when I am there.
The cycling. It's amazing. It's scenic. it's functional. It's just great.
The work. It can be tough. Especially if you're in a creative field. I'm a graphic designer, and while there is a lot of work available, there's a lot of competition. I hear it's similar in other fields to. However, Craigslist exists. So be prepared to use it to find work.
The drugs. Portland has a drug problem. Don't let anyone say it's not that bad, because it is. If you're into drugs, cool; I am not, and it saddens me often. Portland has the highest teenage heroin use in the United States. Meth is here too, but, that's just the Northwest. You'll see it. I hate it.
The homeless. Never bothered me really, still don't. Saw a homeless man giving another man an HJ in front of a public fountain in broad daylight last week, which pissed me off because there are kids that play in that area, but that's not an everyday thing.
The folks. People here are good people. There's the yuppie *******s that act holier than thou, but they are very easy to ignore, in favor of the large amounts of great people you will meet from all walks of life. This city is diverse, and it only takes an hour of walking around to realize that. If you're willing to talk to strangers, you will make friends everywhere you go.
The beauty.