I think important context here is that no matter what the details added were, it always had this aggressive tone of “I’m taking a break and breaks are IMPORTANT”. Which I agree with, but it felt like it was almost aggressive/accusatory, and more importantly: this person was without a doubt the meanest, cruelest, least understanding and empathetic person I’ve ever worked with who ran her staff into the ground with urgent demands and expectations.
Like, I don’t feel confident enough to do it myself, but the OOO writer is probably a known Quirky Person and I admire that to an extent.

Same, I think it’s patronizing to talk people through their options as if they can’t make a decent choice without having their hand held every step of the way. There are plenty of people who can’t, of course, but I don’t think a long, verbose message is necessarily going to help.
A Day in the Life of an Autoresponder. Digital marketing guru Ann Handley has become legendary for her humorous out of office responses. Getting an auto-reply is by definition impersonal, but Ann turns a cold response into a friendly conversation through some clever personification, while also promoting the event she’s attending.