The iPad is my favourite computing device - and the new design the Pros got in 2018 is just damn gorgeous.
I'm a sucker for upgrading, but since my 2018 Pro 12.9, the only desire I've had is maybe switching to the 11" for a bit more portability and one handed use.
Gotta say, over 2 years later and the Pro I'm using still feels incredible as a device. Really not tempted by much, even mini LED. I think OLED would definitely change that though.
The other thing, all along there's been the rumour of mini LED display for the 12.9. I was a bit nervous that maybe with the iPad Air 10.9 that the 11 Pro would go away. But sounds like this isn't the case. If the current rumours are true, that the 12.9 gets mini LED, but at the cost of adding more thickness, I'd myself be tempted to go for the 11.
In all seriousness, what I'm really hoping we see along with iPad Pro updates is a new iPad mini based on the iPad Air (and Pro design). I think I'd grab one of those to use along side my 12.9. And then of course, come 2022, I'll replace them both with an OLED 11" lol.