My twin brother (w & a)and I have been smitten with the wine and watch bug. I agree with all the comments above.
I wear a Rolex that belonged to my father as my daily timepiece. I have a Tag for travelling and holidays, and a Audemars Piguet Star Wheel
for special occassions. Other than the Tag, the others are not in your brothers price range unless you buy from a reputable jeweller second hand.
I find watches like art. It's hard to buy for someone else. It's a very personal purchase and I think you have to try them on before making any commitment.
I'm interested to know what he settles on. I'm sure it will mean something special in any event.