My Girlfriend and I went to Portland a few weeks ago. I have to say that I wasn't very impressed. It is probably the last time I make a special effort to go down there. It wasn't like the city is a horrible place to be, it just wasn't particularly worth a trip. I was glad to go once, but wouldn't go back again.
The best thing about the city was that it was in Oregon, and therefore had no sales tax. Even though I would probably advocate replacing our income tax with a national sales tax, it was still nice to do some tax-free shopping. It was especially nice to have tax free dining since Seattle has an even higher tax on dining out than the normal sales tax.
So what didn't I like about the city? Again, it wasn't any one thing. I didn't like that the city wasn't particularly clean. Many of the buildings seemed kind of run down or old. Even the hotel we stayed at, which is supposed to be one of the nicest in Portland, the Governor, seemed kind of old. Besides that, there wasn't many things to do except to go shopping and there weren't any real sites that you had to go see. The pickings for restaurants was pretty bad as my girlfriend and I couldn't find a decent non-chain restaurant.
The other thing I didn't like about the city is that I didn't feel particularly safe. We walked around at night trying to find something to do (more on that later), and went through some neighborhoods that I didn't feel particularly comfortable walking through. It's like that in most big cities I've been in (with the exception ironically of NYC) so maybe I shouldn't be too hard on Portland.
And then finally, if you don't want to go to a strip club (there were an inordinate amount in Portland) or go tax-free shopping, there wasn't a lot of interesting things to do. Most major cities have something you have to go do or see. Didn't feel that way about Portland.
So overall, it was a disappointment. Glad to cross it off my list, don't think I'll be heading back.