OP: Please take me with you!
Eugene for now, maybe Portland down the road.
Wow, I am so envious of you, moejoe! I would so love to drop everything and just go, but two cats and school are making that option out of reach for me (at least for now). Good luck!
My limited experience with Oregon is that it’s an…interesting…place. Not really bad but, oh, you’ll see I guess. Eugene is quite pretty, however.
In any event, it’s a rare opportunity to get to walk out of an old skin and put on a new one. Enjoy!
Good luck! I don’t have a ton of advice, because when I moved hundreds of miles, I stored all my crap at my boyfriend’s place before I signed a lease and moved into my own apartment. It’s nice that you’ve lived there before, because it takes away the sense that you’re moving “away” from a place. You’re moving “to” Oregon and “to” a new life, not necessarily “away” from the old one, and that’s wonderful!
I loved Oregon when I visited - I’m jealous!
Both nice towns. I’m down in Southern Oregon, myself.
Yes, I’ll take whichever one will have me 
I remember feeling kind of secretly lucky when I lived there before, I’m looking forward to feeling that way again. It’s a bit warmer in the southern end right?
If you go far enough, yeah. The coast isn’t much warmer, nor is Eastern Oregon, but if you’re on the I-5 corridor, there’s a sweet spot in the Rogue Valley that’s much more like Northern California than Oregon. The winters are still cool and rainy, but the summers are uniformly sunny, warm, and bone dry. I’m in Ashland, myself.
I’d plan on spending the next 10 years in Eugene. It’ll be at least that long before there are any jobs in Portland again.