good points.Phew, after days filled with hard work, I'm officially back to the boards.
Let me give away what I think about the possibilities of a time skip.
Let's consider the time skip...
First, I don't think Naruto will go into another travel outside the village to train with a new master. The possibility is that, if he goes... he'll go alone to fulfill a personal quest or he'll be at the village during this time. I consider the reuse of something already used before as a excuse to go to the same result as a weak storytelling. If kishi already used the excuse of naruto going to train outside the village, using it again and again for the same purpose will lower the overall quality of his manga. It's like people saying that someone needed to use life transfer jutsu to resurrect hinata.
A time skip usually isn't short, it's about 2 or 3 years and sufficient to show the growth of the core characters. The process of time skip, specially at visual story like a manga is hard and needs time. You need to decide the growth of your characters, his/her new outfit/appearance, techniques and personal development. Now, everyone from naruto's generation is 16 years old (17 in the case of gai's team - or is it just neji, I don't recall this correctly), so a 2/3 years will put them at the age of 18/19 (adults). This time, having adult core characters opens more doors for the story.
Now, the possibilities of why there won't be a time skip...
Looks like everyone around the face of naruto's world is on his/her way to konoha. Bee, Sasuke, those three ninjas from that village I don't recall the name.... far from that, I don't think Madara will wait more years to capture the kyuubi. So, considering all is going to happen soon, I don't think we'll have time for a TS.
(I'll try to find a better to way to explain this part, for now I believe it's sufficient for general understanding.)
I agree, there is still just too much to be done before another time skip, and seeing as everything that needs to be answered is starting to be revealed they won't throw in a time skip before they finish letting us know whats going on.
If another time skip is coming, it won't be till everything is wrapped up. And the only things that will happen after would be Naruto becoming Hokage and showing everyone's children etc...