Tapered Extrude Problem

[mcobb]

I've probably been working on this extrude problem for several hours now. I'm starting to worry I'm not going to come up with a valid tapered extrude. I know imported dxf files can be problematic in Fusion 360 but I just dont' have the luxury of this information coming to me from Fusion 360 natively. I need to put a 4.36 degree tapered extrude on the sides of the trench that makes the images. Can anyone tell me what I'm doing wrong. I know if one tapered wall face is "consumed" by another before it reaches the floor of the trench it will cause an invalid operation but I can't see where this is happening here. I can get the extrude to work with a taper of 3 degrees but 4.36 is not working. I'm burning a lot of brain cells on this one. The outline was originally made in Rhino. I've take the dxf export and opened it in Autocad to sort out some issues. I've tried converting the polyline to arcs. The answer might lies in one of these operations but nothing I've tried so far seems to make it produce. Of note: When I have excluded the bear from the extrude operation it works! Any help is greatly appreciated. 

https://a360.co/2Ppjq5e

[HughesTooling]

I don't have time at the moment but I've attached a file I use as a template for embossed text that should give you an idea how to setup the 2d op to give a taper.

This is a semi finishing before finishing with engrave.

[mcobb]

Woah, I was wondering if I could avoid the whole modelling issue and suss this out with smart toolpaths. Thank you so much for the tip. Yes, the 4.36 degree angle is the taper of my bit. I'll let you know how things progress. Thank you for taking the time to explain all this.