I’m not a pilot, but were I to imagine that I were my dream plane would be the cancelled XB-70 Valkyrie. What an absolutely phenomenal plane, in every respect. Commercially, it would be cool to fly either the Concorde or the Concordski. The Caspian Sea Monster would be neat, too, but that’s just a WIG aircraft, and learning how to fly a helicopter would be fun.
I used to drive by the Goodyear Blimp’s landing area twice a day on my commute. I called Goodyear once to enquire about becoming a blimp pilot. The good news was that all you need is a Commercial Mulit-engine rating. They’ll get you the blimp rating. The bad news was that the most junior pilot on staff had been there 20 years and counting. Apparently once you’re in, it’s too good a gig to give up.