Watches aren't an investment, no matter what the Rolex marketing department would like you to believe. You should buy a watch because you love it, not because someone told you to, or because of what other people think of it. A $40 Timex will keep time better than a $2,000 Omega (or a $20,000 Patek), but that's not the point of a high end watch. A mechanical watch is more on the order of appreciating beautifully crafted clothing. A $4,000 suit will only resell for relatively low percentage of its retail cost on the Bids and Sales forum here on SF, much in the same way that a $4,000 Omega/Girard Perregaux/whatever will on Timezone's Sale Corner. (Granted there isn't the watch equivalent of RLPLs at Woodbury prices, but ignore that exception.) As far as features, there are some things like a sapphire crystal that are just a baseline mark of quality, much like buying Goodyear welted/Blake Stitched/etc shoes and shouldn't be considered optional. My personal preference is for an automatic watch with a display case back because I like seeing the movement, and would much rather have 1 better watch (or pair of shoes), than 3 fashion watches/shoes, but you should just look around on the various manufacturer's websites, or vintage forums and see if there's something that you fall in love with. Otherwise, what's the point?