Most of Toronto cleans gutters twice a year. The Bluffs is different. The math: Cliffside, Birch Cliff, Cliffcrest, and Scarborough Village sit under one of the densest mature tree canopies in the GTA. Silver maples drop in October. Elms drop in November. Helicopter seeds in May–June. The leaf load is 1.5–2× the GTA average. Twice yearly isn't enough on tree-heavy Bluffs streets. Schedule late spring in April to clear pollen drop and any winter debris. Mid-summer in July to clear helicopter seed accumulation and early-summer leaf shed from sick or stressed trees. Late fall in early November is the critical one — clear leaf drop before first hard freeze. What skipping fall costs in the Bluffs: a clogged gutter on a Cliffside silver-maple-shaded home will overflow at the wall, water tracks the foundation, freeze inside the gutter, ice creeps under shingles, melts into the attic by January. Fascia rot starts within one wet winter. Squirrels and wasps nest in the warm clog through winter. Average gutter cleaning in Scarborough is $200–300. Average Bluffs ice-damming repair is $5,000–15,000. Why we know: Thirlwell's home base is in the Bluffs. Most of our trucks roll out from right here. Dozens of Cliffside homes, dozens in Birch Cliff, dozens in Cliffcrest. We've seen what skipping looks like.