UD,
Man your life sounds a lot like mine except mine started a lot earlier than your and was in the evening, but I am a night owl anyway.
Glenn Miller was still the popular style band when I was in high school and my first band was in that style, but I found out being a band leader less fun than a band player. Buying the sheets, stands, getting folks to practice, renting the dance hall, hiring guards, ticket sales, on and on was more than this kid could handle.
My folks sent me to the University of Michigan as a music major - when I found out that the curriculum was to make me a high school band director, I quit and enlisted because the Korean "Police Action" was nipping at my heals - stayed in through Vietnam.
Bill G