Switch to new Apple Watch series 5
Let’s say I get the Apple Watch series 4 now, when the series 5 gets released, will I be able to trade in my series 4 for the series 5? Has anyone ever traded their series 3 for a series 4?
Apple Watch
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Not for free. You can trade in your Series 4, and get a gift card with the estimated value of your series 4 which you can then use to buy the Series 5 (if and when it is released). You will in all likelihood need to add some extra money to cover the price difference. In other words you won't get a free upgrade to the series 5 if that's what you are asking.
See here: Apple Trade In - Apple