When you say "strip off all the old paint", I wouldn't. If you're thinking of getting back to a natural wood finish, pretty tough if you sand into the veneer let alone the crack repair. You can give it a try. I did a canoe repair recently and I painted a fat angled stripe over the repair from the shear down and around and up the other side to match. Came out nice. Just got my first compliment at a lake on the "nice canoe".