Well, I don't know what watches does he have for now; but if I were to put myself in his shoes, I would recommend 3 watches of the following genres :
1) Dress : Rolex Datejust, period. You could wear it for meetings or functions, and it wouldn't be out of place. It was a classic design that had lasted the trials of time, and would continue to do so, IMHO, for many, many years to come.
2) Diver : Rolex Submariner (40 mm), Tudor Heritage Black Bay Burgundy Red (42 mm), Tudor Pelagos (42 mm), or Omega Seamaster Planet Ocean XL (45.5 mm). Depending on your size preferences, you could pick any of these watches and you would't go wrong either way.
The Submariner would be the de-facto classic piece but the thing was, everyone else seemed to be having one (whether genuine or otherwise). Size was a tad on the small size by today's standards for a diver's watch.
The Black Bay Burgundy Red had a touch of vintage diver, while the Pelagos was an unassuming tool watch. Both were good choices but movement snobs may prefer in-house movements compared to the ETA 2824-2 movements used in both watches.
The Seamaster Planet Ocean XL had the size (and therefore, very visible watch presence), with a touch of sportiness yet toolish appearance. Could be the best compromise of the above concerns.
3) Aviation : Bell & Ross BR01, period. You must pick the manly BR01 in 46 mm footprint, not the more sissy-like BR03. Any series would do as long as it was the de-facto BR01. Macho couldn't be more evident here.
So there you have it, if I were to retain only 3 pieces of daily-beaters, these would be the watches in my watch winder.
LOL, I have the exact 4 pieces that you mentioned. A Rolex Datejust, a Tudor Black Bay, an Omega Planet Ocean 8500, and a Bell&Ross BR01 Heritage.
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