Sure you can do this with Mach. As DaOne said before he lost faith, this is only a three axis job, you just need to bend your mind a bit to see it.
Let's forget the "pre-trimmer" - this is just a dumb tool dragged along by the X axis. Also forget the fact that the stock is spinning - that's of no interest to Mach.
So, that leaves us with the X axis with the 2 tools attached. The first tool is the Y axis and the second tool is the Z axis. To help see this, in your mind just rotate the second tool round the X axis by 90 degrees.
Now the real mind bender. Imagine a toolpath for the Y axis - it's just a profile of the job but so is the Z axis but staggered to the left and rotated by 90 degrees so standard CAM can handle it. Then you generate an engraving path. I used Rhino for the pic attached. It's supposed to be a baseball bat - hey give me a break it's not bad and it's late and the beers are doing just fine.
Cheers
Ian