I wouldn't worry about repointing the bricks right now. They don't look bad. You do want to seal the cracks in the cap though. What happens is snow will settle on the cap then melt during the day and water seeps into the cracks. At night it freezes and pretty soon the cap starts breaking off. Go buy a good extension laddar (not a cheap one it will scare the hell out of you) and get up on the roof and seal the cracks in the cap.
Then finish cleaning the gutters.
For those who understand no explanation is needed, ...For those who don't none will.