+1 Nanuq.
If you are looking to retain value, a vintage Rolex that you like is the best answer. Unfortunately, there just aren't that many watches that hold their value (or increase) like a vintage Rolex.
Or buy something that doesn't cost nearly that much so you don't have to worry about it, and use the rest of the money for something else. Based on some of your description above, something like an Omega 3573.50 would fit the bill. You can get it with the Mitsukoshi panda dial, and it has an exhibition caseback with an interesting movement. That dial is rare, and you should be able to find one for under $5,000.