I think that the more boxes you have, the more overwhelming it gets, personally. I hate hate hate how complex the AI War lobby is, when it's for a midcore game. It's fine for AI War, but when we start splitting things out that's where this heads. The AI War lobby once only had like 10 settings, but now it has what feels like 80+ (whether or not that is actually true I don't know, as I've not counted it).
In terms of having a lot of difficulty options, the core thing is: is this so overwhelming that someone new is not going to try it? I think the answer is no, because it starts them on tutorial and they then just play that first. If they aren't inclined to do that, they probably aren't midcore gamers.
Once they've played the tutorial, they're much more acclimated to the game and the list of long difficulty options shouldn't bother them. But as it stands, all those extra options are all hidden inside one difficulty dropdown.
I'll be curious as to the thoughts of others, as I'm obviously too close to it to be of much use in evaluating it. But that has been my thinking.