Three things. Choose 3-tab asphalt shingles. Get at least three competitive quotes. Schedule in late fall when contractor demand drops. In Ontario that combination can bring a 2,000 sq ft replacement in at $7,000 to $9,000 all-in.
3-tab shingles carry a 15 to 20 year lifespan. Adequate for budget-focused projects, though architectural shingles give you a better cost-per-year-of-life number for not much more money. At the quote stage, don’t cut ice and water shield or ventilation. Those aren’t optional. Premium underlayment and designer shingle lines are where you can trim without affecting structural performance.
The most expensive part of replacing a roof is materials at 40 to 50% of total cost. That’s where the real savings lever is. Scheduling is the other one. The best time of year to replace a roof for competitive pricing is late fall, not peak summer. For a full breakdown at different material tiers see how much it costs to replace a 2,000 sq ft roof in Ontario.