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If he was on a 19 seater or possibly a regional jet $16k-$20k would not be unusual for a pilots salary ...
I know people who pay thousands of dollars a year for the privilege of being able to fly.
SO my guess is it wouldn’t be hard to get some really good pilots to fly a local airline for $25,000 a year. Especially if they had a business on the side that runs itself, it would be a great way to get to fly around without having to spend your own money.