Hmm . . . .090 - one of the heaviest and most vibrating powerheads there are.
Perch and clamp the mill on a ladder between two saw horses ( just like it was going to be cutting a log) and stand and take a photo directly behind the mill and level with the bar
How much wobble (up and down) is there in the powerhead.
Even a little movement will cause the bar to move up and down especially with the 090 vibe.
The weight of the powerhead will make the "down" amplitude bigger than the "up" amplitude which could be enough to cause the bar to dive.
You could try and provide some support between the mill uprights and then down to the 090 trigger handle (connecting to the wrap handle won't do much).
Something like a SS wire and a large turnbuckle might do it.
View attachment 448484
It also looks like you have removed the dogs?
If the 090 dogs are on that very heavy powerhead is really going to be hanging out in the breeze and cause a worse problem.
If your winch is pulling directly on the log from that position then this will contribute to the problem by constantly tipping the mill during the cut .
Have a look in Will Malloff's book on Chainsaw Lumber Making about how to attach a winch to a mill for minimum tipping.
Short bar on an 090 should not need a winch at all if the chain is sharpened right.