Are you guys new to all grain or did you come from BIAB? SOunds like youre not setting the grain bed, and just running off your wort thru the tap too fast in generall... Good things take time yaknow
Um so with the vourloauf, go very slow, im talking a Litre/Min for the first few. This get the flour and small grist stuch throughout the grainbed and not all pulled to the bottom.
With your whirpooling I use whirlfloc to clump that sutff together and drop it. Even if you dont have it, Whirlpool with spoon/paddle, then let it sit for 30min to all drop into a cone. Then once again open up the tap slowly so its not dragging the trub (hotbreak/hops) in. I dont have a robobrew, but if the tap has a threaded pipe (1/2" i assume) buy an elbow and point it up, this way it will not suck up the trub, yes you will miss out on a litre or two. If you put it sideways you can make it whirpool with a recirc pump easy peasy. Anyway you can experiment with ideal placement.
Im assuming you dont have a recirc pump (i just got one, its a cool toy and worth the investment)
So now even if you screw up filling your fermenter, rack of the top into your keg, all those hops and break settle in the fermenter. Theres no way enough should've made it into your keg to block it. I have a glass carbouy so i can easily see when activity has finished and time to transfer/bottle. If you have plastic, get one of those "sediment reducer" make sure the slit is pointing up and it will not suck trub off the bottom of the fermenter
Hope some of this helps