Marc
I can call you on this question directly to discuss the right approach if this doesn't answer your question
From what I can see in your example drawings is that the Z call outs are on the right angled lines - but those lines should be curved corners (front of gutter as you call it) - and so you really need to transfer an elevation to the PC and PT points of the new curve that you want to insert and to do that I would use the method as shown in the PUG 2.0 Training materials in Exercise 99 (at the base of this link)
You need to use the Incoming / Outgoing slope to compute the Z values at the PC and PT points and then sideslope will work well from that linestring with the PC and PT elevations and the curved corner using the offset of the front of gutter. Just watch what happens to the elevated point at the right angle corner when you add a fillet curve of the right radius on the corner - you may still have that in the curved line and you should likely delete that elevation and set it to ? *undefined" and then just carry the PC and PT elevations into the model.
Let me know if this helps / if not we can do a call later today to discuss
Alan