My neighbor's cedar siding looked fine until a storm last fall. The wind got behind a spot where the paint had scraped thin and peeled off a whole section. That repair bill was over two grand. Normal wear is one thing, but ignoring it is how small problems get expensive fast. You really have to check it before every winter.
Is it bad that my idea of trimming is just hoping the wind does it for me? That plan has not worked out great, clearly. Guess I should actually use those clippers.