I've seen TWOK a lot too, though nowhere close to 500 times. Maybe one twentieth of that.
I've seen TMP close to thirty times. I've seen all
of TNG and DS9 about twenty times, and every episode of the other series close to ten times (I don't skip).
I've seen Data's Day
probably more than any other episode or film. It's not my favorite, and it's certainly not the best, but I've always felt it perfectly encapsulated the entire franchise.