Do we need to talk to Naruto about this first, since we're already supposed to be collaborating with Oro on this? But even if so, we definitely don't need to talk to him before we talk to our advisors about the deal right? In fact there's probably benefits to talking to them before we talk to Naruto.
I mean, we
could go ahead based on Asuma's authorization and make the deal on our own and only tell Naruto about it after the fact. And that doesn't sound like the
most objectionable thing. But I think Naruto would appreciate it if we took this current issue of strategic importance to him first, both because as Hokage it's his job to make decisions like this (such as, say, judging whether the context has changed enough to rule differently from Asuma) and because it shows we respect his authority enough to turn to him for direction.
If we did Orochimaru first and then turned to Naruto and said "I didn't want to risk you overruling Asuma's authorization" it would just sound like we were scheming to get the outcome we wanted, after all.
And you're right that it would probably be ideal to have our optimized Orochimaru game plan figured out before talking to Naruto about it, especially since said optimized game plan might wind up including Naruto's help, but I get the feeling that the QMs will want us to put in the work of helping create that optimized game plan alongside our sanity checkers instead of just saying "make the magic happen", so getting the optimized game plan is going to require a substantial amount of plan space. That's why I figure we do this next cycle, since we can chain that into executing the game plan with no delay. It's a touch awkward still, but I think it still works if we get general permission from Naruto and then (if we decide to enlist Naruto's help to make this work) come back a few hours later with a refined plan for him to agree with. All in all, it'll still work out, I think.
The degree to which how catastrophic Pain's return will be for us has so many diverse fail states that I cannot help but feel that we should avoid it as much as possible. If we do nothing with rift research from now on, Pain returns at his full power, and assuming Akatsuki's solution allows for Pain to come back from the dead indefinitely Pain will effectively become the new god emperor of mankind. If he returns in such a matter with our help that may positively incline him towards us but we would have to explain ourselves to everyone in Leaf why we betrayed them for a bunch of mass murderers. If he returns and we tried and failed to stop him... we would have to deal with an angry and motivated demigod among demigods wanting us dead (which is oddly nostalgic as he would become effectively our newest Zabuza or perhaps Yagura).
I do not mean to disbarge your perspective. I simply find it quite unusual and I am curious as to how you came to it orginally.
Yeah, like, it's just, "Pain becomes the god emperor of mankind" sounds like kind of a win condition to me. Not as good as Omnikage Ami, let alone Hazou/Goketsu/Uplift supremacy, but I think there's a pretty good chance Pain's rule is just objectively good for the world. He'll inherit AMITY, a peace-enforcing power structure that feels like exactly the sort of thing he was trying to create originally before giving up and resorting to his grand ritual (which I don't think he can repeat, with the first three bijuu appearing to be permadead).
There's a fair amount of uncertainty left in the proposition, of course, but, like, by all accounts this is a man who wants to save the world as much as we do, who has the power to make entire countries balk, and godlike charisma that sounds perfect for the current battleground that is AMITY diplomacy. I give it pretty good odds that the world with Pain back looks a lot like it does now, but with Akatsuki working as a more effective force for world peace and AMITY further reinforced until it really truly is more than just another postwar treaty.
As for Pain specifically coming to hate Hazou... I have a hard time seeing that. He might in an abstract sense hate that we came around when we did, just in time to ruin his plans by inventing skywalkers and such, but we're a kindred spirit, "rarer than hens without teeth" as Itachi put it. As far as necromancy goes, we haven't especially done anything to indicate that we're trying to block Pain's resurrection, since all we did is make rift seals and we have a very tangible interest in resurrecting Jiraiya and Akane. When we were talking with Itachi about recruitment, we didn't even come across like we particularly objected to Pain's return (and indeed, one of our leading plans was the Ami-coordinated "life-debt with a resurrected Pain" gambit which for all intents and purposes still involves a resurrected Pain). I think Pain would have to learn very specific things about Hazou in exactly the wrong order to come to the impression that Hazou is an enemy, enough that it doesn't seem all that likely to me. Maybe if we provably go all-out on stopping his resurrection and get caught doing so, but in that case the rest of Akatsuki has already killed us for violating their dimensionalism ban so it's a moot point.
Overall, I just have this sense that we could've been Akatsuki in another timeline. If we went Hidden Heaven maybe, staying a non-village-aligned ninja force with monopoly over the power of flight, perhaps we could have wound up talking face-to-face with Pain and finding a true kindred spirit. If we didn't tie ourselves down to Leaf, if we hadn't bet all our everything on Leaf being the future of the world, we might have come to decide that the Akatsuki was the best route to Uplift instead. Not that I regret taking this route, especially when it gave us Jiraiya as part of the family, but I view Akatsuki as our enemy out of circumstance, not out of true ideological difference. Even where we disagree on the finer points, well, I figure Pain would've enjoyed talking with us about Uplift, this ideology so similar to his own yet born of completely different roots, championed by another ideologue who can't help but see how horrible the world is and how much it needs to be fixed. I think in time what disagreements we do have would largely resolve themselves through earnest dialogue.