Just hit this, anddddd it results in not only a perma-fail of the quest but also prevents you from the getting "The Wasteland" achievement/trophy. Luckily I had an extra save before I finished this quest.
Notes (how to fix, and some notes for the CDPR to debug):
1. Originally, when I started the job Dakota thanked me for a previous job I completed.
2. I had been having similar issues where Regina would thank me for old side jobs when starting new-unrelated ones. Something something - I think your queue of audio messages need to get flushed sometimes instead of the first one just being taken off the top of the queue.
3. My *sorta* fix for this requires 3 side jobs. First I completed (Gig: MIA - it's among the greenhouses in the fields). Then tried the Trevor mission. As a result, it triggered both audio messages instead of just the first one. If you don't get both audio messages you'll definitely fail at the end of Trevor. Unfortunately this alone didn't cause the mission to complete so I had to at least start another job - Gig: Good Bye Night City. Not sure if the audio messages will catch up at some point or if they'll cause another quest to fail though.
Edit: Finished all jobs in the badlands - still can't get the Wasteland achievement, and the last gig I had is stuck in an "incomplete" state even though it's actually done. Also note, I'm on PC. I saw that in 1.04 a similar bug was fixed on xbox.