A general trend- Big/far-away needs less headroom than small/up-close.
I am able to safely push levels considerably higher at larger PA amplified performances and when recording from farther away. The overall level in those situations may be high, but dynamics are relatively constrained. In contrast, I need more headroom, a whole lot more, sometimes more than I expect, when up close to small ensembles. On stage in close proximity to a drumset the peaks can be extreme. It's the inverse square law thing - close brings high dynamics, and also the difference in untamed acoustic energy direct from the instrument verses the same having been managed through a soundboard and reproduced through the PA.
However, the repercussions are not the same. They are in a way, inverse. Brief acoustic transient overs or limiter-engagement from a close/sharp/acoustic drumset "crack" are less likely to be obviously audible than slower bass-heavy driven overs / limiter-engagement of content through the PA that is much more likely to sound obviously distorted.
I do hear a significant difference in level settings that do not produce overs when I listen back to my recordings, yet after I even everything out in the DAW I hear far less difference, if any. I want my peaks comfortably high, yet in determining what "comfortably high" is in a particular situation, I might also consider how much "foot-room" I have at the bottom in combination with how much "head-room" I'm leaving at the top.