CrimsonEclipse,
Are you single? Anyone else you need to take care of?
If the answers are yes and no, then you're as prepared as you can be. It sounds like your not mentally prepared. It's like jumping in a pool, except you can climb out later if you need to.
As I've posted elsewhere, I'm going through an amicable divorce. Once my wife moves out, and I finish settling with my old house (20 miles away) I'll be selling my truck. That will be this year.
In them mean time, I ride to work every day. I take grocery trips on my bike.
I live near the central part of Louisville and can ride to almost anywhere if I change jobs. I don't know where you live in Portland, but I'm assuming it's somewhere central. If not, at least you've got better public transportation that I do.
Have no fear. Just do it.