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What's the typical (if there is one) career path for getting to fly a C-21A Leerjet, C-37A Gulfstream, etc. for DoD members, politicians, and other important people? Are only cargo/heavy pilots given these opportunities?

Recently, I was placed on probation by my squadron leadership. My AOC told me to inform my parents about my probation during a formal meeting (SCRB). It would not have been appropriate for me to respond that I had no intention to tell them; informing my parents would damage our relationship more...