I have noticed that most software does the approach to the part with G41 or G42 with a single move. I have always done it with an additional very short (0.010") straight move after the G41/42 but BEFORE plunging in with the Z axis. I don't like the compensation being applied after the cutter is in the material as it often cuts material I'd like to keep. When trying to apply cutter comp to a small pocket the single move method may very well destroy your part. The way I do it the cutter goes right into the pocket. I also like to use a radius on and off the part, as the entry and exit points are not visible that way.
Another thing I do in the design phase of a part is I never make the inside radiuses on size for a standard end mill. I typically design 1/4" radiuses as 0.260". When cutting with a new full size cutter it sweeps the corner with clearance and doesn't chatter. When someone else designed the part with a 0.250" radius I usually grab a reground end mill and sweep the corner that way. At one shop I worked at I became very popular with the tool room guy because I was always asking for regrinds instead of new end mills.
Gary H. Lucas