the two hills I will die on in tool design are "make error messages as good as possible" and "every option you add imposes a comprehensibility cost"

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the two hills I will die on in tool design are "make error messages as good as possible" and "every option you add imposes a comprehensibility cost"
I'm curious what you mean by the second part? I usually view configurabilty for users as a necessity, but there are definitely ways to make badly designed configs.
In a lot of design situations, a decision needs to be made. This is the heart of design. A naïve designer will often say "just make it an option!" and there are certainly some decisions for which this makes sense, but there are many—probably most of them—where the approach that makes the tool most usable is actually to just make the right decision and not allow it to be configured. A tool with 100 options is far less usable than one with fifteen or twenty. A tool with 1,000 options may as well have zero for all anyone will ever be able to comprehend them.
Interesting, much to think about! I suspect I'm quite unusual with how I use computers, I'll happily sit and work through long config files or settings pages to see what everything does but I guess most end users aren't like that.
I have recently found Firefox's settings menu to be lacking, but the about:config page is much worse to actually use. Admittedly that's a rather extreme example but this is definitely something to ponder on for next time I need to design something.