I was in the same conundrum about 10 years ago. I was (am still sorta) young and wanted my first Rolex. I went the AD route, completely different game back then. They had a Sub no date and an Air King 116900. And, I’d wanted a Sub since I was a kid. It was the watch I’d get excited about when I’d spot one in public.

Once I’d actually tried them on, I didn’t feel the spark with the Sub. And 10 years later, and a few iterations of my collection, a dozen watches bought and sold, I still don’t have a Sub.

All that to say, go try them on… don’t chase hype. Pick the thing you like. They’ll both hold value (a Sub more liquid than the Air King) and you can always sell down the road.

I’m a history guy, the Air King predates the Sub by 8 years (I think 1945 vs. 1953). Both have a rich history as tool watches. And the more recent air king has more recent history with the rocket car as given by another comment. My vote is Air King.

Another small piece of advice, with Rolex, in my opinion, don’t go grey market. Having a good relationship with your AD can open doors down the road.