...I know I'll end up hating myself for asking this, but how do you " waste a headset" by "turn down the toprace 5 degrees too far" ?
I honestly don't get this, but I'm all about not compulsively servicing bearings that don't really need it before they do. For the record, I run my headsets pretty tight.

It's more or less a stationary bearing (for all practical purposes, IMO). So with hardened races and bearings, my assumption has been (for quite a while now) that if the front wheel will flop under its own weight, that's about how tight I want it in operation. There's no way I can do that without the occasional overly tight headset (front wheel won't do that). Which I then back off. What am I missing in all of this ? How exactly am I damaging anything ?