So, I think this is a mistake here. If you give him most of the centre to freely march through, he can absolutely bypass the Kirschenholz by sticking to the Rotholz area. The Kirschenholz is relevant in so far as we put a firing line in the middle, allowing for ambushes on Sarnscheid.
Yeah, this is also a criticism I have. Why Guillory and not the 55th? As a Defensive Genius, they are the safest option to choose for the risky job of taking the forward position.Though I have two concerns regarding your plan, one is why send Guillory to take Rotholz Turm? The same position could be taken by the 55th and 108th, without risking taking horse artillery ready fire as Guillory does when moving from the west.
Using Guillory for this also weakens the Western flank. I disagree that he can bypass the Kirchenholz if we have cavalry operating in those woods. If he ignores the Kirchenholz, Guillory and our pathfinders can threaten his flanks and his backline, including his cannons. The pathfinders on their own are a much smaller threat, since without cavalry support they are very vulnerable to being ridden down by his cavalry.