Hey,
I was in the same boat. Do yourself a favor and skip on Tag. If you want to get an Omega, go with a gray dealer or used. Amazon.com or Bernardwatch.com will have good prices on Omega.
Rolex Sub is iconic, but it was not for me. Stainless steel Submariners will retain most of the value over time. Combined with regular price increases and the fact that you can almost always flip it at a good price makes it a good first choice. But do yourself a favor and try all the watches first. After looking at many watches I actually prefer GMT-IIc over Sub, but that is my choice.
One more thing: It is all up to you. Whatever marketing gurus have come up with is irrelevant. You can climb mountains and dive w/o a Rolex watch and many people have done just that. Go to a store, try watches, get the one that you love the most.
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