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At your price point IWC is probably the best time piece you can get your hands on but you'll have to look around. Guys often swap out of watches regularly so you can find something with minimal wear with warranty left. Until you step up to the real big boy stuff (Jaeger, Patek, etc) nothing is really going to improve in value. I've got a lot of watches in my winder and I reach for my Aquatimer most often. Love the thing. A PO IWC will hold better than almost anything I know of. Vintage you're looking at possible mechanical issues, $ etc.
One other thing to mention about the Aquatimer in particular is they licensed quick release strap from Cartier. You literally press a clip and the bracelet comes off and you can put on the rubber strap. I change mine almost every day, it's really like having two watches in one.
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