Since buying a watch is so dependent on personal taste, I would do it this way. Start with a watch box, and include the same watch in all options. I would have the watch on its bracelet (or OEM rubber strap), since they can be tough to get later. The options could be: upgraded storage box, different strap options (either more straps, higher end ones, or NATO/Zulu/quick change etc). You could also throw in a watch roll/strap change tool/spring bars. I also like the idea of a watch analyzer/timer, it's something I'd like but probably wouldn't buy myself.