Birth Year Watch Recommendations - 2008

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@marcnorthThe GMT II was introduced in 2007 -- so maybe that is an idea, a Pepsi GMT. That would be a safe way to go, and would inherently retain value (and will definitely appreciate by then).
I agree that this is kind of a no-brainer for what you are looking for and personally I would be over the moon if I got one.
I do like the Speedmaster Alaska project cause it would be more special, he could always get a modern Pepsi...

A few other options maybe?
What about the Omega Seamaster Planet Ocean from Quantum Of Solance?
It's kind of a collectors memorabilia and I want to believe it will retain it's value or go up, it is not as "flashy" as the Rolex (which may be a good thing?) and will cost less.

The Deepsea Sea-Dweller was also introduced in 2008

And if money is not an issue how about a Daytona Paul Newman? It was not introduced in 2008 but he (Paul) died in 2008 🙄
 
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Really great thoughts -- including the Deepsea Sea-Dweller, Ref. 116660 (3900 m) https://www.hautetime.com/rolex-sea-dweller-deepsea-best/61170/ Thanks!

As I am not a Rolex collector (which, interestingly enough, may actually be a reason to consider a Rolex for him), I would like Rolex aficionados to weigh in on their thoughts on the following options:

1. 2008 GMT II Pepsi - 2nd year of issue
2. 2008 Milgauss (Green Crystal) - 2nd year of issue
3. 2008 Deepsea Sea-Dweller (116660) - 1st year of issue

The other in the running so far is the 2008 Omega Speedy Alaska Project. Welcome thoughts!!
 
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Bumping this up for some more recommendations and feedback. Thanks in advance. M
 
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As one of the younger people on this forum, the Milgauss would be a great option.

As well as being a more unique Rolex to have (NOT another bloody submariner or a Datejust), the antimagnetic function works perfectly for a young person who spends his time on mobiles, tablets, and other magnetic instruments.

IMO his personal preference will not matter as much, it will be more important that the watch came from you. That was my experience when my Dad gave me his Sinn 356. I would never have chosen that watch for myself, but It is the watch that I am the most emotionally connected to now.