Two crashes I see don't seem to have much impact, one in screen shot only shows tool kissing wall by .002 or so and the other is about .01 deep if I compare visually.
When I pull away slowly, I don't see any red marks on stock which suggests to me that collision is minor and would not result in tool breaking if you run file as is.
Two crashes in adaptive tool path seem to be result of lead in and lead out or tool retracting policy and maybe they can be avoided by fiddling with options in linking tab.
One thing I would change is using bull nose for roughing and finishing, resulting in smother transition between levels.
