I personally see no issue with this as long as all accounts are logged into one side.
In all the time I have spent flying with FT, I have never seen him intentionally bomb and bail to avoid any type of combat but in fact will stick with empty buffs just to shoot you down.
Most of my kills on him are actually from him bailing. If he has already WF the town and strafed the guns down he will bail. I'll attack him while he is shooting guns, but after that it's not worth it. 90% of the time my pilot is shot by the first ping. I'll keep an eye out for his troops while he chases me around. Once he realizes Im not going to engage his bombers he bails to get a new set or try a different base. I can avoid his shots if im porpoising but that takes away my ability to shoot back. I'll bait his shots with that if I know someone else is going to make a run on him. As soon as your plane flies straight for the length of time it takes a .50 to travel you are dead.
He wouldnt be able to train a friend or family member to have his skills, imagine if he gets a good paying job and starts a train of 10 sets of bombers all with insta kill gunners.
You can have an army of accounts doing work for you, and if you are at prime time you have one or two people defending.
And this guy testing dual boxing by flying both formations as one, imagine Finetime linking two sets of B17s together 2ft apart....he'll be landing dozens of kills on anyone that comes withing 1.5k