Seriously though, how we portage is going to depnd a lot on who is on the trip and how many there are.

Solo, I usually take the canoe and a light pack first and come back for the heavier pack with the daypack across my chest unless I suspect the portage is unusually tricky.  Get the heavier load across while fresh.  I sometimes triple towards the end of a long day of portaging.  Just depends on my energy level.  Safety trumps speed, always.

When with my usual paddle partner Tim on 2-man trips, we generally single the portage.  I get canoe and light pack, Tim gets monster pack and daypack.  All incidentals are strapped into the canoe or onto a pack.  We'll do about 100 rods at a time and then take a 10 minute break before resuming.  The 10 minute break usually happens at any point that looks more interesting, flora-wise and I'll use the time to photograph and just enjoy the woods around me.

On trips with 4 or more, it usually takes a portage or two to evolve to the system we'll use the rest of the trip but then we stick with that system in order to maximize efficiency and ensure that everyone knows what they'll carry each time so nothing gets left behind.  2nd to last load scouts the landing to be sure that nothing is left behind except that which the last person usually carries.  If there is anything that was forgotten, this person either carries it or reports it to the last person when he meets him on the trail so that person knows to get it.  Last person does one final sweep of the landing before loading up as well.  Never once have we had to go back to retrieve a forgotten item with this system.

I'm always in hiking boots for a portage and I wet-foot it. I'm not into balance beams or rock-hopping with a load on my back, either.  Plow through!