Yes, a small one (less than 1 year)
Yes, a medium one (between 1-2 years)
Yes, a big one (more than 2 years)
I think a timeskip only would be suitable after Akatsuki's destruction, including Pain, Madara, etc; Between the first time skip, Akatsuki wasn't that active, and probably the jinchuurikis weren't captured; ONly in the beginning of part 2 Akatsuki has begun with its activities and moves, and right now, they won't stop until they capture Naruto; so a timeskip right now is out of question;
If things keep this way, the world's gonna be destroyed in this quest for Naruto, and we must deal with Akatsuki, Sasuke, the kage's summit before a new time skip. I'd say Narutoverse would be prepared for a new time skip only when the peaceful times come, and I can assure you, such times are far away from our hands...
after the summit war is waged and a skip cna be placed there
or maybe after sasuke makes his move and another sasuke vs naruto battl
a few years skip and the war is still raging thats when naruto comes back to complete his destiny and change the world forever
i think there may be a time skip after the kage meeting and the pain puppets getting beat. but the real pain will still be alive for a while. i think naruto is going to talk to the elder frog and he will tell him to travel the world like jiriaya did to start his path as the destined child and start making a name for himself. he will travel for a couple of years and maybe learn about his heritage before he leaves from tsunade, and he starts in the old whirlpool village or whatever it is called know. and he finds about his mother and her techniques and also tries to master the kyuubi with the scroll frog. it won't be another series but it will be like when goku left at 15 to train with kami and he then came back at 18 to fight in the tournament. i see naruto doing something like this to find about himself and grow up and gain experience. imo
I am leaning towards Danzou's coup forcing alot of Konoha to go rogue, including kakashi and naruto, or something of that nature. After that, certain things will occur, I still think Naruto is going to meet Kirabi and help him control the Kyubi and I don't think Naruto will take out Pein/Nagato, but he will remain a menace. After some more development I can see a timeskip happening.
Personally I would love to see another TS, but.. but from, I think, objective point of view it's rather not possible at this point; actually manga will wrap up with everything with the end of part 2. Besides Kishi-sama at volume 47 stated that his in his finishing plot<?>, so.. yeah. Besides I think that at the end Kishi may have give us some TS, but only to show how characters made their future or sth like that <if he will not do an "open ended" ending ^^>
I really like the idea of a timeskip, and I hope it would be shortly after the Kage meeting, either because of a war, or because Naruto flee the village so that he's not used as a weapon to fight Akatsuki.
I'd like it to happen, but the plot is already progressing, and Madara just said "Let's begin the plan", so I don't see why we would have a timeskip right now...
If there's one, I predict that it will be after chapter 482 and that we will see Minato Gaiden before getting to Naruto something-else.
That would be nice, no?
1-238 - Naruto (238 chapters)
239-244 - Kakashi Gaiden (6 chapters)
245-482 - Naruto Shippuden (238 chapters)
482-487 - Minato Gaiden (6 chapters)
488+ - Naruto "something-else"
That would be neat!!
You know, before jiraiya died, he never had any idea of fighting a full scale war. All he cared about was getting his friend back. Then pein came along and sorta made naruto understand that war is way more terrible than he ever imagined. Not only that but also the conversation with minata made naruto understand how deep the whole thing was. Naruto has taken his whole messiah complex fairly well and recently has started preaching to the world that war is a bad thing.
Now, the whole "naruto will stop wars" thing was an interesting development for the story but I do feel it was forcefully included and to some extent random. The way I see it, naruto knows war is bad and he knows the pain of losing people close to him. Yet, he has yet to experience a war. For the plot to actually make sense, IMO naruto needs to face a full scale war and be an important part in it. During the war naruto could gain prestige in the ninja world and get an understanding of what he is constantly preaching against recently. Getting to be known would avoid situations such as the one involving the raikage where naruto was blatantly and not so kindly ignored and morally bitch slap. It would also be awesome to see naruto fighting a war sasuke started. In any case IMHO the most ideal development the manga could have would be a timeskip were naruto really participates in what goes on out there.
I think there will be a timeskip. The reason is simple: I think we are meant to see Naruto in action as a shinobi in his early 20's. It would be so awesome to see him as an adult like Minato was in Kakashi Gaiden.