Not that I have that much gen Rolex but they are all pre-owned of course.
A 2001 14060 is a great choice. It's modern, has lugholes which I love (14060 always have anyways).
Like USMC said: why put 2K more for the same watch but new knowing that it will loose value the minute you exit the shop.
As for papers or guarantee....
I came to the conclusion with the help of my dealer and some great friends of this forum that it doesn't really matter.
Original papers will raise the value of the watch when you buy it or when you'll sell it.
Say +500$.
But is it really worth?
I don't think so as if you service the watch at Rolex you will pay the same amount of money and get a certification with their service papers.
I have one without papers, and others with complete sets of papers, box, goodies.
It's up to you in the end. If you can get a full set, it's of course nicer.
Buying online?
I bought them all on line at www.subgmt.com (a pure online dealer, with no shop)
I also trust the german sellers on r-l-x.de
As for US based sellers, a lot of them are very respected.
I never dealt with Monster time but I don't see why there would be a problem either.
Cheers
Stephane