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Common and Boring could be attributed to several of the iconic watches from various brands. Maybe I'm wide of the mark but I always understood that whilst a new Speedmaster/Black Bay/Luminor etc would initially drop a bunch of money after purchase, an equivalent Rolex would retain it's value.
They must be made in similar quantities with similar specs so why would it be that one is more valuable than the others even though the others are also classic designs from brands with a similar heritage.
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In a word, demand.
The market views Rolex as the definitive luxury watch. That maintains demand to a degree that totally surpasses all other watches. Unlike something like a Patek they're also fairly achievable price wise.
(I think you can also include a Speedy)
They're also fairly good about controlling their value and grey market. It's not like a Zenith which can always be bought at a discount.
I'm sure a brand new Rolex would hold its value as % slightly better than the alternatives you mentioned, but it will still depreciate to start.
Because their greatest faults are ironically their greatest strengths.
common : widely desired / large market
boring : continuity of design
A few years ago it was almost mandatory for a man's watch to be 42mm. Now everyone is lusting after "heritage pieces". Unless he has some sort of unique expertise in consumer trends, picking the equivalent of a Tudor sub will be luck.
Just to confirm is he going to wear it or put it in a safe?