Hi Wayne - at Ross on Wye we've started conditioning in the keg (though we use keykegs, not polykegs. but same principle applies), and have been doing so successfully since last September. It's only a year's worth of experimentation (16 batches totally around 5000L off the top of my head.)
You could fill the keg by gravity but it would be slow, and I'm not sure you'd always completely fill it. We fill by attaching a coupler to our racking line and simply pumping the cider in. You weigh at the end to be sure it's full. Keykeg sell this kit:
https://www.keykegshop.eu/keykeg-filling-head-incl-manometer-335/ - but the key thing here is really the tap, to ensure the cider doesn't siphon back out as you remove the coupler.
Yes, we dissolve the sugar (or do it pet nat) and ensure it's properly mixed before filling. We do not monitor the conditioning at all, but we do check each keg is ready before the first one goes on sale. We have a DIY keg dispense setup in the cider barns for this purpose.
You could add too much sugar, there is always that danger if you make a mistake. However the pressure capacity of these kegs is seriously large, much higher than you should be reaching with conditioning. So that's a fairly low risk. Keg couplers/lines also have built in pressure safety valves that will act as failsafes in the dispense system. You can reduce this risk by taking measurements for priming sugar seriously. But if you have never had a problem in a bottle, there's no reason you'd have one in a keg.
We add more sugar to our kegs than to our bottles for two reasons. Firstly, as kegs are usually served chilled, you need a higher volume of co2 to achieve the same effect of 'fizz'. Secondly, customers drinking cider out of a keg tap expect bubbles, whereas in our bottles we can get away with serving something closer to what we think is ideal - there's less "fizz chasing"! We've been experimenting with different varieties of apple with different amounts - between 9g/L and 11g/L. However to be honest, the variance you get from conditioning means I feel there is a fairly large room for error, and a bit of inconsistency between batches. I don't consider this a huge problem in terms of drinking or customer expectation, as it's part of the point of it being a live, natural product, but it can cause difficulties for publicans/whatever so it's something we're still iterating on and trying to improve.
Hope this helps!
Albert