To wit: we have a number of files that are imported extremely widely and each contain 1000s of constants, type aliases, and enums. I think the idea that "this will make it easy to reach for" has been appealing, but when you start doing dependency analysis or wanting to split up stuff that relies on this, you find yourself in real pit. It's still not clear how we can divide all this stuff up without creating a ton of circular deps.
I don't think either of these two mentioned extremes is a great idea, but I understand the impulse to tend towards #1, even though I hate it. I don't know what automated analysis should be run on these things, but do think some common sense reasoning of "do these things lumped together have a similar reason to change?" is a decent razor