I’ve started a Meetup.com group for us at http://www.meetup.com/wordpresswinnipeg/ ! It’s probably horribly broken right now in some way but I’m sure it’ll get better.
The bill for Meetup.com comes to $43.20 every 6 months. If you’d like to chip in, find us a sponsor, or just buy me a beer towards that, that’d be awesome. Also, if you’re in the donating mood, why not donate to the WordPress Foundation or contribute to WordPress?