He's going to pick up a sense of humor after his best friend dies? Nah, man. Nah. Their is nothing wrong with the current cast just their attitudes, the only person who needs to die is Merlyn. He's serves no purpose, is too OP, and knows too much. He should never have even been brought "back to life" his character has accomplished nothing, they could have easily reintroduced the League without him.
I image it'd be a gradual process, not "Ha, my best friend just died! Isn't that a hoot?" It'd be an event that would allow Oliver to grow up and try to look at the good things in his life, which is what had Diggle always wanted for him.
And let's be honest, presently Oliver Queen doesn't really exist, and neither does Green Arrow. There is only The Arrow, The Vigilante, The Hood - unless you accept that this Arrow is the Green Arrow of this universe as he was intended to be, which, fair enough, makes up for that part of the equation, however, Oliver Queen at present is simply The Arrow pretending he's not The Arrow and Oliver Queen instead.
Every death of someone close to Oliver thus far has affected the way he conducts himself as a crimefighter. If Diggle were to die, then I think it'd only be appropriate that it would effect not Green Arrow, but Oliver Queen, whom Diggle knew better than anyone.
We've seen in the flashbacks that Oliver used to have a sense of humour. It'd be nice if that part of him was resurrected.
I'd kill off everyone but Diggle and Ollie, maybe keep Laurel around but not too frequently.
Honestly, Ollie accepting the league offer (at least temporarily) would be the best thing ever for the show and the exact change it needs (but we all know he's not going to)--change of status, new setting, potentially new characters, new intrigue, etc... Ollie needs to just get away from the goddam arrow-cave for a season or two.
Roy and Laurel are pretty much teflon for at least two seasons each. Maybe they'll replace Roy with Mia Dearden, but I don't think they'll go for that.
Of course Thea
could die, thus leaving Oliver on his own, Connor notwithstanding, but I don't think it's necessary for her to die.
Felicity isn't going anywhere for a long time. She is the darling of the show, it simply isn't happening.
It's kind of amazing some of you guys got through the first season at all, much less up to the third. Thea, Roy, and Laurel are the best they've ever been this year -- they're far more measured characters than they were at the outset, they've grown a lot, and are actually useful to the plot now instead of being completely tangential whiners.
Thea, Roy and Laurel weren't as front and centre in the first two seasons, which can be a bit of an issue when people want to see Green Arrow do his thing and not give his ever-growing number of companions a play by play as they second guess his every decision or make decisions via a committee.