Re: Wood Stake Bed Sides?
Mainly on the canoe carrier:
It would be pretty easy to set threaded rod coming out vertically from the tops of the stakes, then have a couple of cross pieces that you could drop on and wing-nut in place. Depending on how tall you want the sides to be, you could make the front risers taller than the rear to keep the front of the canoe from hitting your cab. depending on the setup, I'd worry about the canoe achieving takeoff speed unless the bed sides are locked in place. You could also strap the canoe straight down to the bed tiedowns, that would hold it all down at once.
As for bolts/screws, I totally vote carriage bolts. They'd look nicer and hold better.