I've been boarding for 25 years, I can ollie @ least 3 feet on a snowboard.
I have never been able to ollie on a skateboard, I don't even try anymore.
I'm the exact opposite. I've skated all my life, and know the mechanics of an ollie. At the same time i'm just not seeing the height expected to feel good about it. My only thoughts are that speed is required, or i'm not actually flexing the board since i'm only about two season in and my not be able to tell?
p.s if helps i'm riding a full camber mid flex board.