For Milton, we just sent the town an email for the ward boundaries :) We update representatives using scrapers hosted on
ScraperWiki.com. I'll write one for Milton today.
I only mentioned the municipalities relevant to WardRep in the last email, but Represent more generally has ward boundaries for 67 individual municipalities and representatives for 22, plus all municipal representatives for BC, AB and QC. It also has both boundaries and representatives for all provinces and the federal level. It has an API to make all that information available.
James