Ok, so think I have it now. It’s not super clear but you MUST buy a 2nd plane and have the 1st one set to crew ‘ON’. You can either fly other missions in the 2nd plane or just ignore it but the first crew will go off flying. So it seems to work but that has introduced me to the 2nd issue :).
Off goes the crew flying their missions:
1- They earn 20k income for a cargo mission (quite low I believe).
2- They trash a good landing gear causing 30k in maintenance.
3- They incur another 12k insurance (I chose the middle option).
It’s only one days data point so I will patient and see how this develops but I somehow don’t think making a loss leading career mode is a particularly intelligent bit of game design.
At least on the good side, I have figured out the pilot mechanic. I have seen some people on forums say they got it to work with only having one plane but must admit to be somewhat sceptical of that given my experience.