I think the key point is practice. I'm new to this and obviously not retiring anytime soon from it lol... But Im trying to think of it like my old radio show I had back in the late 90's. The first few months were pretty much the same show complete with playing the same songs over and over bc I had no idea of the library literally staring me in the face, dead air, no idea what to say on the mic. Around the 6 month mark, the show magically changed. The flow between songs were cohesive. There was never a repeat song in the 5 hour set. I could make jokes and tie it in to whatever PSA I had to read. No stuttering, no dead air. What took me 4 days to plan in the first few months took me an hour or two. It was all practice and comfort and discovering what made people call to bullshit and make request and what made people call to say you suck get off the air.