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My four plus one

 

If I were a seasoned collector I would say to your friend to not get any watches that are not practical for his lifestyle and that he would not be happy with as either “entry-level” or “exit” watches. 


I admire other dials, but this is all the dial I need: 




Then a practical watch with a useful chrono and a clever, minimalistic annual calendar complication (I regret to have let MIH-1 pass):




I would definitely advise your friend to add a German chronometer that could be used as a smart-casual dress watch:




My fourth recommendation would be an understated technical beast:





And a perfect plus one:



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