>And there's probably a lot of fun, harmless things to bet on. eg. "Will Conan lead an extravagent musical number at the Emmys?"

I cannot fathom what could be fun about that.

Fun to lose to insiders on the production team?

I don't know why you'd ever put money into something like that. Anyone working on the show will know the answer

Kinda legal insider trading, I guess.

I mean, what's fun about my specific example? Guaranteed money.

By that definition all terrible aspects of the concept are the same as the fun.

Conan hosted the Oscars.