I'd love to see more Felicity/Digg interaction. I really like their friendship and I think that they understand each other in a way other characters can't. They're quite aware of each other, and there is absolutely no way that I can believe that they didn't get close during those five months. It's one o my favourite aspects of the show, and I really hope we do get to see more of it next season.
As for Roy/Felicity, I do hope that there is some fallout for Felicity. I agree with you guys that I don't want it dragged out, but I think it will interesting characterwise for pretty much the one big lie Felicity told to bite her back. Felicity is not a liar, and she doesn't manipulate people, and if she had lied to Roy about this at any other time, i.e. not just before they were about to battle, then it would certainly have counted as manipulation.
@ArrowLimbo The more I think about it, the more a five month jump wouldn't work. There are way too many conversations to have, Oliver/Laurel, The Team/Roy, all that about Quentin.