Patek Philippe

mgwagman
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I have had the 5296 and now have Rolex DD in Platinum

Greetings from Chicago also.   On the 5296 I sold it to buy the Rolex Platinum Day Date which is similar to the White Gold president although the platinum day date is much heavier and durable.  White Gold does ding and so does platinum.   On the Patek Philippe it is clear that everything about the watch is of a higher quality.  Price in salvage metal value is not where the intrinsic value of any watch is including a Patek.   The value of Patek is that it is handmade (really handmade) and they are rare and they make only about 30K-40K watches a year.    Patek clearly makes the best of the best watches and are highly desirable and are extremely sought after by collectors.  The pros of the Patek are that it is rare, beautiful, simple, elegant, and no one notices it unless they really know watches. 
       Rolex watches are durable rugged and great everyday watches.   On the White Gold Day Date it is a nice watch although you take a steep hit on value if you pay retail.   The advantage of the Day Date is that it is a heavy wrist watch with a bracelet and you can feel the watch on you wrist.   It is durable and usually you should not have any problems with either watch.    The advantage of the Rolex is that everyone knows what it is (it turns heads) or this is a negative, you can sell it quickly and not lose much value if you paid the right price, it is a timeless design etc.   Rolex however, makes a lot of watches a year estimated at about a million, but when you consider how many watches are stainless steel then the number of all gold or platinum watches must be a fairly low number.  I have to say that I really like the Day Date as much as the Patek Philippe or maybe a little more because of the bracelet, but the Patek was an excellent watch and I do miss it a lot.   I had the 5296 G with the Sector Dial and it was like a piece of art.  The plain dial is elegant and subtle but very classy.   If you like having a bracelet then you should probably go with the Day Date.   However, if you want just a dress watch and you were your sport Rolexes everyday then go with the Patek as you should have one nice dress watch.   Make sure they significantly discount both watches as the resale on each watch is not bad but not great.   A good discount on both would be 30-35% from a dealer, if not go to a grey dealer for both and compare prices.    Maybe you should get one and then the other later.