Hi John,
When I tested in production (the screenshots above were from my test environment), I didn't see outbound on behalf of queue calls in this report either.
I've filed a ticket with development about this, so I think a fix is on the way and this report should include those calls soon, especially since it does seem to include them in my test environment. What you described in terms of your Outbound queue setup sounds correct to me.
I think that you can also set an outbound calling address and name on external trunks that will work even for business user calls (i.e. the ones that are showing up correctly in the report), but I am not a telephony expert, so maybe @Greg Shultz can confirm if that's true?