I now believe, that the crashes could have something to do with what happens when the AI flights return to the carrier.
At least this would correlate to the distance to the carrier the crashes occured at. (Unfortunately I didn't note down the in game time when the crash happened).
On my first try I bugged out as soon as Weed was hit and the order to bug west was given. So I headed directly to the get well and then RTB. I got to under 30 miles from the carrier.
2nd time around I loitered around the get well point for some quite some time as I waited for Cajun and Smoke to get there. The crash happened when I was still about 80 miles out.
On the 3rd time I was again pretty fast and didn't have to wait for the other flight because Weed was hit again. As mentioned in the OP I got to about 42miles from the carrier.
Based on this, I think that the returning flights somehow cause the crash. At least on the 3rd try I noticed the message of a plane trapping shortly before the crash.