What you are experiencing is due to the fact that the first segment in the Follow Me path is not perpendicular to the profile (or the ground plane in this case) The Follow Me operation projects the profile to be perpendicular to the first segment in the path. The end face of the extrusion will be perpendicular to the last segment, too.

The fix is to not draw an arc for the path but instead, draw a circle and split it at the mid-points of sides at the correct angle.

Short answer is ‘yes’. You have to be careful to get the first segment of the path perpendicular to the profile you are extruding if you want the end to be square. FollowMe makes the first face perpendicular to the first segment of the path.

Thanks for the help, I found a decent workaround, BUT!

Now I am curious, there has to be a way to find (solve for) the “Perfect arc” setting?

Using the 2 point arc tool, if i have an imaginary right triangle with

Opposite = 8
Adjacent = 8
Hypotenuse = 11.3137

bulge = 2.5530
or even though mathematically I could find the answer it is further complicated because SketchUps programming converting to an unknown X number of sides based on length, angle, ect,ect,

What? The number of sides used to draw an arc isn’t an unknown. Get the 2-Point Arc tool and look at the Measurements box before you start to draw the arc.