Seven counties, three states

Orange County NY

Hudson Valley proper. Colonial and Victorian housing in the villages, large newer subdivisions around Middletown, Goshen and Warwick, and the Highlands above the river.

What goes wrong here: Suburban roof shapes with long valleys dumping into a single downspout, and mature street trees overhanging the fronts of older village homes.

Ulster County NY

Shawangunk ridge and eastern Catskills. Stone houses, 19th-century village stock, Woodstock and New Paltz weekend homes, and the Rondout valley farms.

What goes wrong here: Historic stone and masonry walls stain and spall fast when a gutter overflows, so the cost of getting it wrong is higher than a repaint.

Central and Southern Sullivan County NY

Monticello, the old Borscht Belt corridor and the Bethel Woods side. Mixed older housing stock, ranches and bungalow colonies alongside new resort development.

What goes wrong here: Older housing with original undersized 5-inch gutters that cannot carry a Catskills downpour, feeding straight into foundations.

Northwest Sullivan County NY

Upper Delaware corridor. Riverfront cabins, cedar-sided camps, lodge-style builds and a strong short-term rental market.

What goes wrong here: Rental owners are often off-site, so overflow damage goes unnoticed until it has rotted fascia. Guards and a maintenance schedule matter more here than anywhere.

Pike County PA

Pocono lake country. Large gated second-home communities with hundreds of near-identical homes under heavy pine and hemlock, plus the Milford and Matamoras river towns.

What goes wrong here: Pine needle and hemlock litter is finer than leaf fall and passes straight through cheap screen guards, so the wrong guard is worse than none.

Sussex County, NJ

The New Jersey side of the tri-state corner. Kittatinny Ridge and High Point, the lake communities at Vernon, Highland Lakes and Lake Mohawk, older farmhouses out towards Wantage and Frankford, and ski-country second homes above Hamburg.

What goes wrong here: Ridge tree cover is pine, hemlock and oak together, so a guard chosen for leaf alone blinds within a season. North-facing slopes hold ice weeks longer than the valley, and a large share of the lake and ski housing is seasonal, so a failed gutter is usually found by the ceiling rather than by the owner.

Upper Delaware, Wayne County PA

River valley and ridge. Log homes, cedar shake, board-and-batten, standing-seam metal roofs, a lot of second homes and hunting camps. Heavy hardwood canopy right up to the rooflines.

What goes wrong here: Leaf load is the worst in the territory and the metal roofs shed snow in sheets, which rips gutters off their hangers and makes snow guards a necessity rather than an upsell.

Lake Wallenpaupack PA

Dense second-home and HOA communities around the lake. Many owners are three hours away in New Jersey or New York.

What goes wrong here: Absentee ownership. Nobody sees a failing gutter until a ceiling stains, which makes guards and scheduled service an easy sell.

Delaware County NY

Western Catskills. Farmhouses, barns, converted camps and a growing stock of renovated weekend houses along the East and West Branch.

What goes wrong here: Long cold season and deep valley shade. Ice dams form early and stay, and undersized gutters back up behind them.