My memory thinks this has been discussed before, but I’m not finding where.
Outline with Outside Only and Wide Cutout, and with Depth First selected, cuts all the way down the first offset before stepping over to the second. Here shown part-way through the preview:
Workspace:
outline-outside.kmz (177.3 KB)
De-selecting Depth First gets usable output. That’s a minor inconvenience to the extent that it messes with other ops that could be combined in one run.
(It doesn’t respect Inner First but that’s not a problem in this instance.)