I worked with a guy years ago who would update his voicemail greeting literally every time he left the office. So the bare minimum would be that he’d record a new message when he arrived in the office in the morning. Then, when leaving for lunch he’d record a new greeting listing the time he would be back in the office, then he’d record a new message when he got back from lunch, then a new one at the end of the day saying he would be back in the morning. That’s not even counting the times he was out of the office on work business. It was deranged, especially since he had the type of job where he would normally be in and out of the office often.
This would go over like a lead balloon at my company, and, were that person on my team, I’d tell them to change it. It does have a connotation of “when I feel like it” about it, and most of my team is not high enough up the food chain to take that sort of stance (and the ones who are high enough up are client-facing and have the good sense not to do so).

I’m with you, honestly! When the end was “she’s So great” and not “she’s so [sime negative adjective]” I was actually surprised. I thought it was annoying and condescending and all around extra. But I guess I see why some people (including the ooo boss) would think it’s funny.
I used to hire a lot (hundreds) of freelance writers who would each be given a deadline by which their particular project was due. As these were large projects, they typically would have several months to complete them. I soon discovered that a significant number of freelancers (at least 25% if I’m remembering correctly) would email a couple of days before their assignment was due to report the sad news that they would be missing their deadline because “someone close to [them] had just died”.