For all the jobs, so far, the actual Boring tool has been mounted vertically, rather than horizontally, as shown, BUT the holes have not been 100mm diameter! (Possibly beyond the limit for vertical mounting?)Which ever way the tool is mounted, use the shortest one possible, to maintain rigidity.
The orientation of the tool, not just the speed, may affect whether chatter occurs.
I can see no immediate problem with mounting the tool "inverted", other than needing more clearannce under the job, to allow the tool to pass through the work piece.
For accurate sizing, the final cutS need to be Spring cuts. In a 25mm deep cut, it would not be impossible to see some taper, otherwise.
Howard