I have an almost identical hardware setup and although it takes a few cycles through various tries to get the connection, I can almost always get it to work. One tip is to make sure you remove the Zwift app from the watch and use the companion app there instead. A key for me seems to be to start riding (ie hit “ride”, but before your event has started), then go back and attempt to pair.
My hardware:
IPad Pro 2018 11 inch, iOS 13.7 (yes, not current, but I’m lucky because this is avoiding the crashing bug introduced in 60239 release and not fixed in 60474)
IPhone XS iOS 14.1
Neo 2T
Watch series 4 (make sure Zwift app not loaded on it)
Here’s what I currently do:
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Start the ride 15 mins before event begins (it does seem to make a difference to do the steps below after hitting the orange RIDE button)
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Try to connect a Bluetooth device from within the Zwift app on the iPad, looking for your watch on the list (rarely works first time through).
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Quit and restart the Zwift Companion app on your watch (look up how to do that, not something I ever have to do for any other app on my watch, and I wonder if this app is the ultimate source of the flakiness), then repeat step 2.
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Quit and restart the companion app on the phone, then repeat step 2.
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Try steps 3 and 4 again, but in the other order.
Just to be clear, I’m not saying you’ll have to do all of these, you might fix the issue at any of the steps and therefore not need to run through the other steps.
Hope this helps, I’m confident you can get it to work consistently. I don’t know where the unreliability in establishing a connection at the beginning comes from, but once it’s going and I’m actively riding, I don’t think I’ve ever lost the connection during the ride.