The last time radio was "fun" for me? Last week's show.
I do a specialty music show at a community-run station, as I've been doing for the last 17 years.
Deeply enjoyable because I pick the music, I structure the sets, I choose what to talk about in the talk breaks, and I figure out where to put the promos and underwriting so they won't kill the momentum of my show.
It's enjoyable to me because I enjoy the content. It's not necessarily related to the technology in the studio.
I remember records having their first few seconds destroyed by repeated cueings, cart decks that needed cleaning every few hours, and phone interfaces that wouldn't work right if Alexander Graham Bell himself hit them with a shoe. I do miss all of that, but for purely nostalgia reasons; I wouldn't go back to any of that today.
Nowadays, my music is 95% from CDs (mostly custom CD-Rs) and 5% from vinyl (yes, we have two working Technics 1200s in the studio, with their own sliders on the board). The promos/IDs are all on a hard drive, which is far more reliable and convenient than cart decks - especially for my 300+ custom IDs. No mp3s for me - they sound like crap in the studio, and our FM processing is gentle enough so that they still sound like crap after going out over the air. (Actual CDs and records sound great, though.) Hopefully, the next generation of hardware will include something with a remote-triggerable USB port, so I can load up a memory stick or portable hard drive with music at home, bring it down to the station and play it through the board.
I'm a big fan of the left end of the dial, as you might imagine. I'm glad I don't rely on the radio business for income - it really wasn't that much fun when I did get paid (late '80s CHR), and it looks like a whole lot less fun today.