I had gunshow tables for some 30 years. Took a lot of rifles on trade. I also bought a fair number of small collections. It was common for me to take rifles and mess around some, tweaking forearm bedding and doing some test shooting to see if I could sell it as a "real good shooter".
I never found a rifle with any obvious problem with headspace. It's most likely worth checking with old military rifles, but modern bolt actions are pretty doggoned rare to be out of spec.
As far as overall length and concerns about pressure spikes, I commonly checked to see how far forward I could seat a bullet before it engaged the lands. Tap the round out with a cleaning rod, recheck a time or two, and I had some idea about what not to do for overall length.
One thing for sure, a once-fired case, reloaded for the same rifle, is about as good a fit as you can get.
I'm mostly a hunter, so any time I regularly tweak the package to get half-MOA with three-shot groups, I'm happy. Benchrest folks have a whole different standard, and certainly can justify following the Brownell ideas...