[dthunt]

It may help to rewrite those in your head to, "as an experienced systems administrator who knows how these particular config files work" or perhaps "how config files work in general".

These are all questions of basic fact and they are all easily testable.

What do courts do when this situation comes up? Do they play warring experts, when (at least) one side definitely wants to perform a test, because they are confident that their interpretation is correct?

(ed: 'questions of basic fact' like, whether a server with this configuration is hittable from non-allowed IPs)

[bitJericho]

That's the judge's job to figure out what the truth is. If needed I've heard a court can hire their own impartial expert.