It's not a question of brands. You'll be lucky to get your
money back on an Air King, even if it is a Rolex. On the
other hand, that old chrono you have may get you six figures if
someone recognises it as a Newman Daytona.
Even with Pateks, there are enough Calatravas about that unless
there's a bit of history behind that particular watch, it's not a
given that you won't be offered less than what you paid.
All up, if you're looking to get "investment" pieces rather than
just collecting them, forget it. There's much easier ways of
making a buck.
Thanks, you sound like you have lots of experience with watches.
Any particular brand and model to recommend with a budget of less
than $300.