As a bit of a Star Wars nerd, I really like the Death Star Tourbillon, but at over $250k AUD (is for the box set, who doesn't what a 6 foot prop box) never happening.
Then there's the slightly more practical ones I really like but still can't see myself ever actually spending that much on. Speedy, Zulu Time, Aqua Terra...
Still got to get my wife on board with me buying my first automatic at the $500-$800 range.
I've got a Junghans Trilastic 17 Jewels that belonged to my great grandfather, so not sure how old, but I'm assuming old.
Still works, no idea how well. Is in dire need of a clean and just sits in my watch box currently.