I have owned a number of vintage watches including Rolex and Tudor. In comparison to other vintage watches I have owned (IWC, Omega, Accurist, Longines, UG, Seiko, Citizen and numerous others) my own observations are as follows.
The Rolex 6694 had a very good and substantial crown and winding, case was good, dial extremely well made, the cyclopes a good addition for reading the date. The bracelet was too small anyway as on most vintage watches and similar to most nothing remarkable. The Tudor I had was basically a date just two tone case with Tudor branding. Like the 6694 excellent watch I found to be faultless. Some of the comments about poor quality I can only assume others have purchased a knackered watch. In comparison to other brands, UG have a very good case and even their gold plate is very thick and isnt likely to chip or fade like some modern junk. Omega are a bit hit and miss and many here have Dennison cases so they could be cased up in 9ct gold. In comparison some Omega watches cases dont feel as substantial as the Rolex ones though like Longines, they movements in quite a few are great quality and easy to service. IWC I found to be nothing remarkable but the workhorse movement is well known and long lasting.
The main issue of contention is the price. Vintage Rolex are around 3 or 4 times the price of say Omega or Longines. Tudor probably double the price. Does the price justify paying? I dont think so however, I did find the Rolex to be a step up from many vintage Omega just probably not 3 or 4 times a step up. IWC vintage likewise dont come cheap (Though dont seem to attract the irrational hysteria that Rolex do) and likewise the steep increase may not be justified.
Regarding modern Rolex. I fail to see a modern steel sports Rolex as tarted up in any way unless you see some bling factor in a steel watch with a black or green dial? Rolex have always had a dress watch line up in the date just and Cellini and there are plenty of gold and two tone of both so there is nothing remarkable there. Sorry all I see is lots of resentment over a watch some folk cant get and just cant move on and get something else. Almost like cant get the pretty girl and while can get someone else its just not the same so have to do and say anything to put the pretty girl down.