1) The Black Bay is polarizing - some love the striking colour combinations (me) - others definitely don't dig it at all. If you don't know where your Dad stands, I'd pass on that one. 2) A safe choice and a lovely pilots watch. I don't find that IWC's ETA / Sellita-powered watches present a compelling value equation (i.e., you can get comparable aesthetics and overall quality for a good deal less elsewhere). Then again, it's a gift, so value for money isn't likely going to impact how well it is received. 3) He's a Rolex man. He owns several for a reason - he likes the brand and likes the product. If you can swing it, this would be the way to go.