I'm really bad with these threads. My powerlevel is decent enough but I'm a plain guy and I watch what everybody else does and like what everybody else does.
As far as TV series go... Recommending Sunred, Boogiepop, Big O, Mouryou no Hako. Sorry, this is really the best I can do. OTL
With shorts/movies it's an entirely different matter. If you like shorts you're gonna look into obscure stuff by definition. There isn't much point to recommending Nekojiru-sou as everybody has seen it but at the same time I feel recommending Tetsuro no Kanata is just as pointless. I think shorts are something you have to dig up on your own to enjoy it to the fullest.