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I use my IWC Mark XV when I go flying as I don't want to beat up my other watches (not professionally, just SEP + small heli and VFR only).
If I was looking for a Flieger chrono I might go IWC 3706 or if split second 3711 or 3713. There are current iterations of all these watches - including the IWC Mark XVIII shown above - but I find them a lot less attractive than IWC's no-nonsense models from the 1990s and early 2000s.
Certainly not cluttered are the Heuer 1550 chronos issued to the German Air Force in cold war times. Then there are the Orfina Bund chronos.
Those should all be around your budget. I am lazy with pics but you can easily find them on Chrono24.
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