When does saving headroom become too much? Or does it?

So, keeping my gains/volumes low, carving out unneeded low end as I hear so much about saving headroom (there, we just saved 3.5 db of headroom etc), my mixdown before mastering looks almost anemic. Putting clipping, saturation, mild eq, compression etc then putting the limiter on it means really cranking the threshold higher than I feel like I should. Would bringing up the gain (in the examples below) +9.5db, which is what the second attachment shows before any distortion occurs, make sense before mastering?

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When does saving headroom become too much? Or does it?