Hmm, well I had a quick look, and my opinion is the "failed" objectives are not working.
Nothing to do with your mission, but I think "Ship X sunk = failed" cannot be used to trigger events. Looking at the objective, you cannot set any time limit or anything else, therefore as long as the ship exists the possibility of meeting the objective remains. Therefore as an objective, it can't be failed without linking it to another variable. So your Transports exist when you reach the map zone, however the objective doesn't count this as a failure to sink them. You could go back and sink them or sink them later on their journey, basically it is open ended.
Now linking this with another objective (Reach Zone) would be the way to try and get it work (as you tried), but it looks like it just doesn't work like that in this editor. Seems to me that the problem with the "failed" is carried over into the events, so those events where you egress and don't sink anything are never met as some objectives are open ended and not met...
It is like a horrid logic puzzle. Note the editor doesn't really have AND OR NOT etc for linking objectives so its not as versetile as other game editors.
No idea if there is a fix for this.
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