The company I work for has no problem with me working remotely. I pointed my boss to RandsInRepose's excellent article (The Pond) about remote workers, so we've started the discussion about things we'll have to work through. Needless to say, I'm incredibly thankful and lucky to HAVE a job, especially one that's willing to keep me around as I move.
My girlfriend is a painter (website; http://daubery.com etsy store: http://hollypaints.etsy.com), and has had little luck finding work in Lakeland. So if she doesn't find work out there it won't be much different.
Paul Graham's "Cities and Ambition" article really hit home when I read it a year ago. It made me think about how deeply where I live affects my quality of life, my future, my happiness, my creativity, my productivity, my resources. Lakeland is a "settle down, raise a family, go to church" type of place. It's not for us. I want to run a software company of my own, hire great people, and be involved in a community of artists, musicians, programmers, designers, and makers. My girlfriend needs to be around artists that don't bullshit, have creativity from within, and aren't in constant competition with each other.
Moving to a new place is going to be invigorating. We're hoping the people we find in Portland will continue to inspire us once the newness of a new city wears off. Wish us luck.
If you have advice, or live in Portland, don't hold back.