So what is a fair price to you? For me it is IWC. Watches are like knives...you paid how much!!?? You are going to open a big can of worms. To me, the first time you try on the "right" watch you know right away. Just like picking up a knife the first time and knowing it has to go home with you without hesitaition.
Other lines in the Oris price range: Omega, Fortis, Sinn, Bell & Ross. The Rolex will usually hold their value during resale. Most people will not recognize the high end watch brands. To most people, Rolex is the top of the line for noticing the brand. Wear a watch you like, not for the bling factor.