The IWC 3777 is my ideal pilot chronograph, but struck out by your budget. I took a look around, but oddly enough there seems to be a lack of pilot chronos at this price point. Weird. I'd recommend the Steinhart Nav B chrono but the models tend to have something that puts me off: blue hands or weird pusher/crown design choices. Oh well.
Anyways, if you can manage to bag a Seiko Gen 1 RAF pilot's watch you have something you want to hold on to forever, this is definitely one of my favorites https://corrvintagewatches.com/product/1984-1st-generation-seiko-raf-pilots-military-chronograph-with-nato-issue-numbers-on-the-caseback/
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