Currently i own a dive,field,dress n 2 digital watch. N would love to add a chronograph into my collection. Personally i really like the look n display of the chronograph. Im still new to this hobby and still discovering new stuff.
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You could get a Sea Gull 1963 for less than $500, and it is a 38mm mechanical hand-wind chronograph. Another option might be a Tissot PR100 Chronograph, a 41mm swiss quartz chronograph.
Mechanical Chrono for <500USD msrp is a tough one. Either go for a used watch, you should find plenty for this price, or you could go with a quartz one - also not hard to find, or one that comes to my mind is a Sea Gull. But don‘t expect too much from it... I think a Chrono with a Valjoux 7750 based movement would be the best and especially a solid choice.
Check out Just One More Watch on YouTube. He’s reviewed quite a few chronographs that cost less than $500.
Another vote for the seagull 1963, else if you can live with quartz, some of the Dan Henry chronographs are cracking value for money. IIRC you can see some reviews/comments on Urban Gentry as TGV has a few in his collection.
#urbangentry
The Lorier Gemini might be a good pick and is right at $500
Baltic Bicompax 002 if you're into the 1940's aesthetic:
https://baltic-watches.com/en/products/bicompax-002-black
I would look into the quartz side of things.
May be fork out a bit more for the seiko solar panda?