Homeowners who treat this as a one-time project tend to end up back in the same reactive cycle a year or two later. Tying pre-winter prep to a specific, memorable trigger, like the clocks changing, or right after the first cool snap, makes it much easier to keep on a consistent yearly schedule rather than something that only happens after a problem already showed up. If holiday lights are also going up around the same time, it's worth doing the gutter check first, covered in .
If you've been through a rough winter before and want to avoid a repeat, that's also useful information for us during an inspection. Knowing which specific spots gave you trouble last year lets us focus extra attention there rather than treating every roofline the same.