The bright green (or yellow maybe?) line going right across your S, where you see the extra line in your carve, is a travel move. Travel moves aren’t supposed to cut anything. Easel has your detail bit clearing out the top corner in the S to a depth of 0.24" (why not 0.25" as in your design?..another issue?), but then it only raises to -0.125" before zipping across the face of the S to clear the random spoton the curve of the S. The surface of your S is at -0.125", so if your zero is a little off, it’ll carve on that rapid move.
It’s a toolpath issue…not much to do but tell the Man that you’re carve didn’t turn out. (Or dive into hand editing the gCode…you’ll learn a ton)
As for the other things, I’d suspect a zeroing / squareness / flatness issue…probably not Easel’s fault.