So I remember reading in a few places that the longer you wear certain gear, up to a cap of course, your character becomes more adept at fighting in it, and doing basic activities in it. Though I can’t seem to find anything on it now at this point, is this still the case or am I just insane?
I don’t know who told you that, but they lied.
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like, they totally lied to you, maybe they tried to say that if you fight with more encumbrance you get exp for the skills relatively faster/easier, like for dodge iirc. dunno if its still valid though
Hm, are you sure you didn’t mix up Dwarf Fortress with CDDA?
…well… 
I’ve also never heard of something like this. It’s possible that there is/was a mod, or - as Ragno stated - it was that “helps leveling up dodge faster the more encumbered you are” statement. However, I think that was debunked at some point (unless it has changed since then, I’ve not checked the source code)…
Associated reddit post:
https://old.reddit.com/r/cataclysmdda/comments/733zu2/training_skills_at_high_levels/dnp4jo1/
They probably intended to convey that a particular level of encumbrance is less of a problem once you get your skills up.
There was that comment about how activating a spear strap or similar item to wield your spear or whatever was awkward and slow but that you would improve with practice. Perhaps this is what was meant.