My wife bought my Submariner for me when I turned 30 years old. I always liked this watch and although I would have persuaded her not to spend what she did over 20 years ago (1,500.00) it has been on my wrist for the last 20 years. I believe it is worth 3 or 4 times that amount in todays market used. Although I would never sell it as I plan just to hand it over to my son once I kick the bucket. Which can/is part of the ownership of a unique time piece. I have often had conversations with Rolex owners who where wearing a watch that was handed down from their father of grandfather. Which, IMO, is worth more then any dollar value that you can place on it
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Back then I owned 3 or 4 watches. I had a friend who once told me that once I started wearing a Rolex I would never wear another watch and if I was ever in a $$ jam you could always get something at the pawn shop. Fortunately I never have been in such a $$ jam that I would have to hock my watch butI can say that he was spot on with it being the only watch that I wear. It is the only watch that I have worn the last 20 years and it still looks good after all these years.
I will admit that there are some Rolex's that I would be uncomfortable wearing as some just project an image that is a little "loud".
I think you should practice what you often hear about a p-car, buy the one that you like and the one that you can afford, whether it is a Rolex, Tag or a Timex.