Honestly, it's mostly just dark humor and a bit of financial "exposure therapy". Sometimes seeing the absurdly huge, multi-million dollar number makes the regret feel almost comical rather than actually depressing.
But you are 100% right about the $1k mark. In reality, almost none of us would have held to the top. We would have sold the moment it doubled, bought new iphone and felt like geniuses. That's the reality this calculator conveniently ignores for the sake of the joke!
Appreciate your two Satoshis!