[mike monde]

As an owner of a SS submariner that has been on my wrist for over 20 years, I would say, if you like it, get it. Paid around 1200.00 for it back then, not sure what the value is today and nor do I care. It has been a great time piece for me. I will say that I have not purchased a watch or another time piece since and have no intention of ever wearing anything else. Once I move on and hopefully not in the near or far future, it will be willed to my son. I think one of the benefits of owning one is that it becomes part of you that you can pass along to a loved one. They then can enjoy for many years later knowing it was something that you passed on to them. Rolex seems to have that heritage.
When I was faced with this decision, a client advised me that once you buy a Rolex, you stop looking at other watches becuase your happy with what you have on your wrist. This has been very true for me. So for someone who owned multiple watches at the time, it was a sound investment.
I will say this, I think staying conservative with your selection, like a Air King or a SS sub mariner will keep your time piece "ageless".
Some Rolex's, IMO, can be too gaudy and reflect an image that my be over the top for some.
Like a Porsche,IMO, there are two types of owners of Rolex's:
The ones who own one because they want everyone to know they are rich and can afford it, or the ones who own it because they respect and understand the heritage, the history and the quality that comes with the marque.
My advise would be the same as to someone buying a Porsche:
Get what you like(911,993, turbo, etc)and wear it(drive it like you stole it) and dont worry about it appreciating. The value is in how it makes you feel.