Don't Wait If You Aren't Willing to Pay a Premium
The biggest reason not to wait for the AirPods Pro release date is if you aren't willing to spend significantly more than the current AirPods cost.
Rumors point to an AirPods Pro price of $260. Apple loves to put a premium on the Pro level products and it looks like you will have to pay about $100 more than the AirPods 2 if you want the newest model.
You won't see AirPods Pro deals very soon after the release date, and in fact, we may not see $20 to $30 off until well into 2020.