Pragmatism isn't always the right way. Look at Shimura Danzo. He's said to be a Pragmatist... but look at all the shit he did which only made things worse for the Hidden Leaf Village in the long run. I think trying to harness the Curse Seal isn't the right path, specially since Orochimaru CAN influence those that have that mark on them, making trying to harness it not only not very practical, but insane.
Pragmatism implies that one actually considers the consequences, even unintended ones. Danzo has demonstrated, canonically at least, neither. There is a difference between a pragmatic solution and an expedient solution for a reason, though expedience and pragmatism are often confused. Also, I should have added the addendum that Jiraya would espouse containing it as well, if only to give him time to develop a means to get rid of it if developing a means to use it without the unpleasant side effects is impractical. I agree that pragmatism isn't always the right way, if only because it is impossible to account for every possibility and there has to be
some standards that are maintained.
As for sanity, we're talking about a kid with an obsession with killing his brother and has signs of being a borderline high-functioning sociopath. A trait, mind you, which would be considered
desirable in the kind of society that makes use of child soldiers and assassins. Sane? Sasuke hasn't been sane since the Uchiha Massacre.
What if the time skip results in Jiraiya taking both Naruto and Sasuke on his grand tour? I'm sure the team8!sasuke would not defect to the less competent Orochimaru if he thinks Jiraiya could potentially beat his brother. Also, Kakashi could pull a favor in getting a better counter to the curse seal from Jiraiya.
Perhaps the Sannin Sensei mistakes this lone uchiha as the child of prophecy? They could even travel to see the toads. Sasuke learning sage mode should bypass his need to use the curse seal, or lead him to attempt to exploit it. Cursed Sage Sasuke?
Also, If Pein still runs into Jiraiya, Naruto and Sasuke would have an invested interest in his defeat. Sasuke fights Pein, Naruto fights Itachi, Orochimaru wins?[/quote]
I agree with Dechs that the Child of Prophecy bit is a no sell here, since the
Evil!Authorlord
stated that anything past Chapter 354 in the manga does not apply. That doesn't mean that Jiraya wouldn't have other reasons to bring Sasuke along, though,