Get the quote in writing, itemized
A real quote lists prep work (sanding, caulking, priming), number of coats, exact paint brand and line, and what's not included. "Two coats, premium paint" without a brand name is a red flag — there's a $40/gallon difference between contractor-grade and premium, and you're the one living with it.
Century homes need a lead check
Much of the housing stock around the downtown core and Old South predates 1960, which means original layers may contain lead paint. Any reputable painter will test before sanding or scraping — if they wave it off, keep looking.
Exteriors have a season
In Elgin County, exterior painting season runs roughly May through October. Paint applied below 10°C won't cure properly. Good local painters book 4–8 weeks out in spring — if someone can start tomorrow in June, ask why their schedule is empty.