Late leaves, wet months
The second half of the forecast is where the risk shifts. Phillips expects November and December to be warmer but possibly wetter than normal. In a warm winter, the stress falls on water rather than snow load: rain on unfrozen or half-frozen ground, running off roofs into eavestroughs and downspouts.
Timing matters here. Phillips told CP24 that the unusually rainy summer, capped by the September 2 deluge, has delayed the colour change, and that peak colour could come up to two weeks later than usual, probably after Thanksgiving but before Remembrance Day. Later colour means a later leaf drop, and a later leaf drop means eavestroughs cleaned in early October may be full again just as the wetter November arrives.
What the maintenance calendar says
The CMHC seasonal maintenance calendar recommends clearing leaves from all eavestroughs and checking the roof for wear in September and October, and in spring asks homeowners to check downspouts and make sure the yard slopes away from the foundation. Under this forecast, the sensible version is two passes: a check now while the weather is dry, and a final clean once the trees are bare, before the November rains.
Use the dry October weeks for the jobs that need dry ground: extending downspouts well away from the foundation, and checking that soil hasn't settled back toward the house.
If you're weighing guards to cut down on the second pass, read our look at eavestrough guards and winter drainage first.
Put the final eavestrough clean on the calendar for the first dry weekend after most of your trees are bare, not on a fixed October date. This year, that's likely to be November.