The Logosol mills use a guide on one side of the log. This works well when cutting completely through the log, but not as well when the nose is buried. I have used the Big Mill system with the saw captured by the guide rail and the Timberjig with a wooden rail to quarter logs that are too big to put up on the mill. I always get some twist to the cut when the nose is buried. This is true when using the same bar and chain that cuts straight when the cut goes all the way through the log. The twist seems to always be downward at the tip as the cut progresses. Could be that the rotation at the tip pushes it down, or that the additional sawdust buildup does the same thing, or that minor existing problems with the bar and chain or set-up are magnified by the additional stress. I have not tried cutting from two directions with the log up on the mill, since logs that size are usually too heavy for mill. Once the log is cut in half, I can quarter it without burying the nose. I mark the original cut faces, shim them on the mill to average the twist, cut them from the bottom a little thick and plane the marked face. Lots more work on four boards, but the rest come off the saw flat and straight.
Your idea might be a good cheat for a few cuts where you don't have a long enough bar, but I wouldn't expect accurate cuts and it would be of little advantage when slabbing the log. BTW, if you do cut from two directions, you will gt better results if the tip is only a little past the center of the log.