Do you have the same issue if you follow the OP’s steps to reproduce it?
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Yes I have the same issue and I’m using cheaper insurance not even the premium insurance. Plus it is putting 25% tear on the plane so Mx cost will be losing even more. On top of that I cannot sell any of the planes since I’m just losing money atleast let me sell them and make money flying myself. The career needs tuning in a ton of areas.