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is that going to happen any time soon though? I'd think that if you're going custom you're going to install the seatpost exactly where you know it should be and leave it there until you grow taller or shrink.

Or change your crank length, or saddle, or pedals, or shoes...

It's not really how often you tighten it, it's over-tightening it once that'll strip it. Grease + torque wrench = worth it. You shouldn't need much torque anyway, unless the frame/binder lug is a bit vague/shoddy.