Originally Posted by bing240sx
if you get a mint Rolex with all the paper work, something that MSRP's for $6k - $7k that you get for $5k, you will not have paid too much because you'll always be able to recoup most of your investment easily if you decide to sell it.
a lot of other watches do not retain resale as readily, or at least take more work to sell. Rolex has such broad appeal in North America that it's a safe bet. As is Omega.
Higher end, more obscure stuff like Glashutte, Zenith, etc. have a more limited market (Serious watch douches) and are a bit tougher to flip than a Rolex.
Hamilton is a good entry swiss watch, however, for a starter auto i would recommend Oris. They are the official BMW F1 watch and you can pick them up off ebay, WUS or timezone for great prices, fully depreciated. I made money on my first Oris and wouldnt lose on the Oris that i still have.
however, even though the quality is there with Oris the wrist-presence is not up to Omega / Rolex / Panerai
+10000000000, what he said...
@op: I'd say it depends on how and what occasion in which you are going to wear your watch. For an all around watch I'd stick with a used rolex for your budget. You could pick up a mint gmt or subs or explorer 2 white dial. Or if you want one for a more formal occasion then, save up a little more and get a used jaeger reverso duo grande