Andy! Good to hear from you again and sorry for the late reply.
Here  is a brief history of how we got to where we are: in 2000, we formed  the group Garmonbozia and over the next two years recorded approximately  10 CD-Rs of challenging, cinematic, proggy and almost unlistenable  stuff. Buried in there were some of the kernels that would become the  essence of Blitzen Trapper (Pink Padded Slippers, Texaco, Sadie, etc.).  We played around town multiple times a month and spun our wheels. For  good reason, we changed our name in 2003 and recorded our first "proper"  record - done mainly on a Fostex 8-track, then dumped to ProTools and  overdubbed with Greg Williams, who's become our go-to guy for almost  everything. We had a product and didn't know what to do with it, ended  up not really doing anything with it and continued to spin our wheels.
By  accident, we made Field Rexx - entirely self produced and super lo-fi.  By this time we were wondering what kind of "magic" needs to happen to  get the tunes out there. We began working with a local publicist/friend and  that helped create a groundswell of local recognition. We embarked on a  completely fruitless West Coast tour and garnered our first licensing  deal with a British company that promptly went out of business (as far  as we could tell).
We went back into the studio with Greg and recorded  the working title "BT3" and shopped a few songs around to no avail and  shelved the record. All the while we continued to play Portland and  Seattle, and the crowds grew slowly, but they grew.
Out of the  blue, Eric had written and recorded most of Wild Mountain Nation. We  shopped that around again for quite a few months, got a modicum of  interest from small and medium indies, but no bites. So we decided to  pony up, release it ourselves and hire a real LA publicist. And it  worked. Suddenly blogs were writing about us and the publicist got the  record to Pitchfork who gave it the crown of thorns Best New Music. We  sold 5000 CDs in a week. We couldn't keep up with production and labels  were chomping at the bit. Good problems to have. After courting with  Domino for a bit, we were approached by Sub Pop and it seemed a natural  fit. The rest of the story has been pretty well documented.
During the WMN days, we were approached by a very good booking agent in Seattle  who had noticed the clamor over us. He warned us that if we work with  him, we will need to be on the road alot, like at least 6 months out of  the year. We agreed and have been on his roster ever since - and he's  obviously gotten us some killer opening slots as well as headlining  tours.
Wow - this has become long-winded! Let me boil it down: dominate your local market first - you can probably do this all on your own. Parlay that into regional recognition - for you Chicago is your best bet for getting noticed - and play the shit outta that town and Minneapolis too. Hire a big city publicist that has a good resumé and believes in you - expect to pay a few grand for their services. The more good press you get, the more name recognition you'll have with booking agents that are willing to take a chance and get you an opening slot on a tour.
Hone your songwriting skills, play as many shows as you can in as many places as you can, and if you're good and people like your stuff, you'll start getting offers from places you'd never imagine.
Good luck Andy - hopefully we can hook-up this fall.