JB,
I have little to offer to your post, but because I am an interested party I will share what I think/know by first declaring:
"I am a BobCad V21 user". There!! My confession is now public and complete.
Jests aside, we all know there are better and not as good CADCAM apps out there. I am a relatively new user and hardly competent, but I am able to accomplish what I want without too much pain. I use the CAD portion for my drawings and I find it fairly straight forward, but few of my drawings are very complicated and few have more than a few layers.
Creation of GCode with V21 is OK, but again, I have not worked it very long or hard, so my experience factor is about a 1 or 2 on a 10 scale. I do find the post-processor for Mach3 to be quite spare. I have read that I can augment the BobCad provided PP with my own customization, but have not yet tackled that project. I have not had to spend time cleaning up my GCode. If pay attention to the chains, the Gcode it produces has been quite useable.
I looked at several products but the only one I considered seriously was OneCNC. Nice Product line!! But when it came down to cost and the ability to do the things I wanted to do, BobCad would work and was a lot less expensive. When I got real with the fact that this is a hobby (not how I make my living), I felt my decision was obvious. But the old saw appies: You still get what you pay for.
So, that's what I know. I too look froward to others' feedback. You might also go here and post your questions.
http://216.117.147.20/bobcadsupport/forums/ You have to subscribe but it's a good forum.
Later...
David