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Breitling Aerospace would fit the bill. It has both analog and digital capabilities with a quartz movement. It is offered with a chronograph. I believe it does come in blacksteel and on a rubber or cloth strap. It's probably the perfect watch for a pilot as it will have extreme accuracy, has multiple digital functions that are useful for flight, and is in your budget.
I was a flight surgeon in the USN. I wore a Navitimer during my service, but it's not like I really needed it. I got to fly for fun.
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