One piece of software that I'm eager to try when the Tormach comes is the Freesteel adaptive roughing:
http://www.freesteel.co.uk/ There is an online interface, though they will email you the standalone program if you ask them.
I have done dry runs, but not been able to try it on actual material yet--running TurboCNC on my Sherline mill it pauses at each inflection point, which is counterproductive with the Freesteel algorithm since it is all curves. But the Tormach with Mach2 controller should be ideal for this.
In general, I use Sheetcam for 2.5D stuff (i.e. pocketing, outlining vertical walls, and holes), and Meshcam for 3D surfacing. The two programs are complementary and suit my needs well.
Several years ago I did try a time-limited demo of Visualmill from Mecsoft, and found it easy to learn, though its roughing algorithm needed improvement (it tended to skip around a lot). For an intermediate CAM software, Visualmill Basic at $1k looks like a decent deal.
For 2D I use VersCAD for Windows (I've been using VersaCAD since 1989) and for 3D I use Solidworks at work and the free Alibre Xpress at home.
Randy