I just trim Khloe's toe nails every other week after her bath. I just trim the tiniest little bit off of the end because I once cut them too short and made her bleed
I think Jackson's look okay. They probably could be a little shorter, but as long as they aren't clicking when he walks, I would say you are fine
This may be weird, but I never have to cut Couver's. His nails never grow. I groom him, so it's not like the groomer cuts them... I used to think it was because he would grind them down on the pavement during our walks, but we don't walk on pavement too much anymore. I think he's just an odd duck with some mysterious toe nail deficiency or something... idk