Let's face it, it's not great software.
It is kind of hard to tell from the picture, but I think it would be hard to get a good finish on that part using a planar toolpath. Or any of the 3 standard solid toolpaths in BobCad. I would guess that your machined part has poor quality vertical surfaces and bosses. As far as the roughing I haven't found any logical way to do it, so I usually do a solid toolpath with a larger cutter, with a much larger stepover and plunge (and sometimes change the Material Top to +.05). What type of tool are you using to cut that part? How large is the part, is it real small, a .062 cutter is pretty small? What is your step over distance?