Three of them: GMT Master II (Batman), Black Bay 58 (black), and a Speedmaster (sapphire).
I'm currently hunting for a better job in a similar field to my current one, but which pays better. Once that happens, I can probably get all of them within a year.
My grandfather's gold 1930's Lord Elgin. It's an understated, tank-style watch. I had it serviced, it looks almost like new (kept the patina on the dial/hands), and runs perfectly. I replaced the worn leather strap with a new black crocodile strap. Now it's my black-tie watch that I wear on special occasions.