The unhelpful answer is 'it depends.' The helpful answer is that it depends on exactly one thing you can check from your driveway: what hangs over your roof.
Heavy live oak cover: plan on at least twice a year — once after the winter-into-spring leaf drop, once after the spring pollen tassels finish. Skipping the second one is the classic mistake; tassels mat worse than leaves and do most of the downspout-clogging.
Pines: pine needles slide into gutters year-round and weave into mats that shrug off casual flushing. Twice a year minimum, and homes under heavy pine sometimes want a third pass.
Light or no tree cover: once a year keeps you honest. Shingle grit, wind-blown debris, and the occasional tenant (wasps like a dry gutter) still accumulate, and an annual pass doubles as an inspection that catches loose hangers and dripping corners early.
One more honest note: cleaning frequency isn't just about clogs. Every cleaning is a chance to catch a small problem while it's small. Our cleanings include a flow check on every downspout and a condition report on what we saw up there — because the cheapest repair is the one you heard about early.

