I haven't bought tickets yet, but oscon sure was fun last year in our home town of PDX.

Tradeshows are cool, it's a long couple of days worth of work but you do meet a lot of people. I'm not sure which ones will really help c5 grow with the right crowd. We need to watch our pennies pretty carefully so I'd love to see a brainstorm list on what conferences you guys would like to see us at in 2009..

My goal is to get in-front of as many mid sized (12-50 people) webshops as we possibly can in the shortest possible time...
suggestions?

up here in Olympia, Meetup.com supports Gig Harbor Web Design group, while Facebook supports Olympia Web Design. Both have the approximate attendance that you are looking at. Otherwise, this (https://store.aneventapart.com/#seattle-2009) is a larger event. I am unfamiliar with Portland area groups and events.

oscon last year was several thousand people and a exhibit hall. If we're going to travel at this point, we need to get some real exposure..

the list apart meetings look interesting tho, that's really our crowd more than the religiously open source...

At least one of these:
http://aneventapart.com/

This may be short notice/expensive...but...
http://sxsw.com/interactive