Here's some context for exactly the scenario you mentioned...(only tweaked a little)
Wrangler is wearing his hat (on his head)
He grabs it with his hand
Then throws it onto a hat stand
That would be a use case for parent switching. However, at this level, there is no mechanism to match the positions during that switch, so you're stuck with the position jump.
Although, if you were doing something complicated like that, your better off to just stick with 1 parent, and then use Space Switching (animation technique) to force it go where you need it to go without all the parent switching.
Of course now you probably have more questions about Space Switching (rightly so).
It's where you bake the animation onto a different object, animate it, then bake it back. The baking takes care of the where it should be taking all the parenting and constraint into account. It's part rigging and part animation - it's not something you need to look into right now, but when you do, check out Pierrick Picauts stuff (P2 Design). He has lots of content on this technique.
I think I saw a Phil mention P2 Design on the animation study group chat on discord (I'm fairly certain that's the same Phil who's done the core animation course?).
Yeah, I do have plenty of Q's now, hah. But I'll take a quick look and keep a tab on it for when the time comes!