I'm kind of curious - does anyone with more than 100 hours do a flight plan,
with winds and all, before they fly cross country?

Sure. Especially for long, low XCs. I find it very convenient to have
waypoints, frequencies, "things to watch for", and other stuff all laid
out neatly on a sheet of paper in the cockpit.

One of the additional things I add on my sheet is runway layout and FBO
I'm using. I pre-plan that to avoid surprizes like outrageous parking
fees (which would be free across the field) and such.

Jose
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