HAHAAAHAHAHAHAHA IT'S FUNNY BECAUSE IT'S NOT TRUE HAHAHAHAHAAHAHAHA... >:C

Hinata and Sasuke becoming antagonists, lmfao, boy that would be a shocking turn of events. I won't shy away from these two forming a connection while ShikaSaku and NaruIno are going to occur, but making Hinata a villain would take some freaking work.

Much, much later, yes. I think before a timeskip large enough to bring Naruto back to the village--and trust me, he'll actually LEARN shit from Jiraiya than bigger rasengans and basic tactics-- Shikamaru and Sakura have got to reach a really good point themselves. 

I don't think so. Shikamaru took his lighter and trench knives, but in my headcanon, after he avenged Asuma by stopping his killer, he passed them on to Konohamaru, his nephew. Kid is the only Sarutobi left now, besides the child Asuma left behind with Kurenai. 

I don't think he's interested in a dramatic smut series but I think it might cross his mind.