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To each their own! :) I stuck with the straights for a while and ultimately decided to change, and for me it's worked out well.

The two bonuses are that a) my wife now uses a DE and b) I have a...

I get between 3 and 5 head shaves per DE blade. 3 is a solid number since I switched to DE a few months ago. This is only for my head shaving, mind you. Still only use straights on my face.
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What direction are you going on the sides? I usually did my first past downward (from crown to ear), and then second pass across the side (from eye to ear).

Do you just have the one razor? I...