I'd like to route some pockets to use as sort of a "stencil" or guide to inlay some letters to make a 3D sign.

Does anyone know of a way in the Manufacture workspace to adjust a toolpath to sort of "overshoot" the corners so that my cut-out letters can fit within the pockets? I'm not too concerned with which direction the extra milling takes place (diagonal to corner, along specified axis, collinear with preceding tool direction, whatever), just looking for something to save a little time and "manual labor."

Up to this point, my process has been to manually sketch circles of my tool diameter and make them tangent to an edge and coincident to the corner. This project involves about 40 of these "inlays" and is becoming quite tedious.

FWIW, I'm CNC'ing acrylic for this project, and I only have a 1/4" plastic "O-Flute" cutter. In wood, it's usually not an issue to go back and fill in the leftover radii after the letters have been glued in, since most of the time it's painted anyway. I'm just concerned that in clear acrylic these dogbone fillets (or whatever the proper term is) will be more noticeable.

Bonus question: Does anyone have any recommendations for a good 1/8" cutter for plastics? I'm only going 1/16" deep for these pockets, but the letters themselves are supposed to be 12mm acrylic. I have an 1/8" upcut bit I use for wood, but I'm not sure if that will perform as well in acrylic.

Link to album of reference pics, in case you missed the inlines

This is a client's logo, so unfortunately I don't have much leeway in terms of editing the design to use a curvier font and things like that. There's a level of understanding that we'll get it like 90-ish% accurate, but there's a limit to the degree the client is willing to alter their design.

TIA.