Stowas starts at around $650-$700 for the fliegers iirc. The Antea are still around $500 but I think the wait time is still pretty long. For around the same price, I would look at Archimede if you want a flieger, you can't go wrong with either one though.
all the watches previously recommended are inspired by the german b-uhr watch. and with that $500 budget you can opt for Laco which has history and part of those 5 german watch co. commissioned to manufacture the pilot watch (IWC, wempe, stowa, A.lange & sohne and laco)