I only buy what makes me gasp when I first see it. I love quirky and interesting and for me, personally, that rules out divers and other watches that are highly sought after but that leave me cold. I don't look at whether or not they hold value, but I often shop the secondary market to let someone else take that depreciation hit. The theme of my collection is "things I truly love and happily wear" and there isn't another defining feature. I'm the type who will wear a dress watch with leggings from Target so your mileage may vary.