Great input everyone.
Hopefully I won't be in 8-10 footers for a few seasons. I delivered the boat from Chicago to Milwaukee in a small craft advisory (motoring). The waves were probably 5 foot, but they looked plenty big to me.
Is it possible to look ahead a few waves to plan which spot is best to aim for, or does the profile of the wave front change too quickly to make a difference? (maybe to avoid what looks like could be a breaking wave)
Is it the same idea going downwind? Square-up the stern to the wave as you approach the peak, then head back up to your course? (ie:go over the peak perpendicular to the wave)
Even if you were motoring, it'd been much more comfy with at least a small bit of sail up to stabilize the boat's motion. And if you were motoring in L. Michigan 10'ers, you wouldn't be going against them anywhere fast if anywhere at all. Downwind, close to perpendicular, but not quite... don't want to round down in a trough either.