I think it's coincidental. Let's look at it one by one.
Why Kakashi trained Sasuke was obvious. Sasuke (as he said) was similar to him; he has the Sharingan and has a lightning affinity. It would be ideal to train him, because Sasuke was going up against someone strong and needed Kakashi's attention more than anything else. Plus, Kakashi was more worried for him after the encounter with Orochimaru, worried about how he'd turn out, so he gave him Chidori to 'protect his friends', I think he said. That, and probably to appease him a little with some power, together with some guidance.
Why Kakashi didn't train Naruto was also established. Naruto was too weak in terms of basic skills to learn anything of a high standard from Kakashi. Though he could probably get one or two jutsus down, with his chakra capacity, there's no way he could do anything with fine control. Plus Naruto could never have done elemental training at the time. This already explains why he was passed on to Ebisu, and I don't think there are any other underlying reasons. Oh, and Naruto wasn't as big a priority, given that he wasn't going against Gaara. Neji is strong, of course, but he wouldn't kill Naruto. That and I think Kakashi wasn't worried about Naruto going down a dark path or anything.
Kakashi didn't plan the whole thing out. Why? It would be simpler to just find Jiraiya and ask him to take on Naruto. Just mentioning that he's the 4th's son or someone reminiscent of Minato would have at least got Jiraiya interested in meeting him first. Plus, Jiraiya would probably know who Naruto is by his name. Relying on a plan that had so many odds stacked against it is quite unlikely. And if Kakashi did it not expecting it to work, it'd seem a it...off for him. One thing I'm not sure of is if Kakashi knew Jiraiya was tracking Orochimaru prior to that.
Also, given Naruto's high profile (which is why he was assigned to Kakashi in the first place), Jiraiya would definitely be told about it and maybe be assigned to him if he wanted him. There would be no need to bet on such an unlikely plan.
Well, I can't think on it much right now...but my conclusion is this: it's not impossible, we can't really disprove it, but all it does it fit the circumstances. It's one of those things where things cannot be completely disproved because the details are sketchy. There is nothing in the manga that indicates it's right or hints in that direction, only nothing that says it can't have happened. So while it could possibly, plausibly be believable, it's easier and simpler to believe what we've thought of it all along.