Is this painted cedar siding?
I have painted cedar sif=ding on my home and it requires repainting about every 7-8 years or so. When I repaint, we always clean and prep it real good, then keep a caulking gun of latex caulk on hand the whole time while painting, to fill any cracks like mentioned as we go, then paint right over everything.
If stained or sealed siding with a natural wood finish, I'd probably use a brown or tan latex caulk to match color as close as I could.
Cedar siding just requires routine upkeep, but it looks so nice it's worth it.