Hey Submariner400, I purchased a Gen Sub (date) under very similar circumstances as you. One came up at a good price, with full box and papers and I had to make a decision. I went ahead and got my Sub and here is what I learned.
I learned that the longer you wait, the more your Sub is going to cost. I spent $3100us two years ago. If I tried to buy a full set now at that price, I probably would not be able to find one.
I also learned that because Rolex puts their prices up every year. So I'm actually making money with my Sub. And that is a good feeling.
Having the Sub gives me a good sense of security in terms of cash in some kind of dire emergency. I know at any tick of the clock I could go on eBay and sell this watch for more than what I paid for it.
Now a negative. If that Sub is a 2003, by now it should have the oil refreshed in the works. So if your buy this Sub, at some stage in the future you really should get it serviced. If you have it done by Rolex it will be a significant expense. You could however have it done by a competent watch maker and save a lot of money. Then again, having the service done by Rolex can, to a small degree, enhances its resale value. Now having said this, the Sub I bought had never been serviced. When I took it to Rolex it was the first service it had had in 12 years and it was fine actually.
And all things considered, mechanical watches need to be serviced; that's just part of owning one.
I love wearing my Sub. Where I come from (small city) nobody really notices it for what it is, but I know what it is. The Rolex Sub is really a genesis design and you can see the influence it has had on many different sports watches. From the hands to the dial markers to the bezel, you can see the spirit of a submariner almost anywhere you care to start looking at what other people are wearing on their wrists.
The very few times I