Tastes change. BUT, even if your taste change, connections you have to THE ITEM allow it to stay priceless to you.
This discussion goes beyond watches. As I get older, and I look back at these things and realize that I still have many items in my life that are/were "THE ITEM".
For Example,
My Tom Kuhn SB2. The best Yo Yo I have ever used. But more important, I received it from Tom himself. It was a great day, and all the feelings make the item that much more important and timeless.
Another example, my Citizens Eco Diver that was given to me by my wife on our honeymoon cruise over the millennium, not the best watch by any means, but due to the memories attached to it, I will never part with her.
The memories connected to these things solidify its status as THE ITEM for me. I wish you luck in your search.