Falling leaves and other debris can clog gutters and downspouts, causing big trouble. If the gutters fill with water, the weight could cause them to loosen from the house. Overflowing gutters can cause water to flow between the gutter and the fascia board, promoting rot. Overflowing gutters also defeat the purpose of having gutters. When you finally talk yourself into cleaning the gutters, an extension-type ladder leaning against the gutter is the safest way to get up there.
Stepladders are unstable on soft ground, and working from the roof is just asking for trouble.
The ladder should be tall enough so you can look down into the gutter. If you don't need gutters, get rid of them. If you get drenched by rainwater falling off the roof when you enter or leave the house, you would benefit from gutters. If you have standing water after a rain, gutters can often solve the problem by directing water from the roof toward the street. If water falling off the roof erodes your flower beds, and you do not have a drainage problem, rain-dispersion devices often eliminate erosion.