[felix]

As for their positioning...well when your opponent can gouge a hole out of the Earth that can be seen from space, the "hills to fall back on" plan doesn't really work...

They don't know this; most of them don't even understand the power of the 9 beasts let alone that thing. What you're referring to is suppose to be top secret. At best they know the details about Naruto. Regarding the other jinkiru-whatnot, they are apparently dead or trapped, going by the conversation with the monkey king.

Get a small team of fliers in the air to draw the Jyuubi's attention

There is no airforce as far as I'm aware, unless this is some filler you've watched, which probably shouldn't count anyway. Them being in the air is of no use anyway; there's virtually no cover and we have no evidence to suggest any reasonably effective flying jutsu (other then Deidara's bombing runs).

then get a small team working beneath the ground so that they can immobilize the Jyuubi's movements

Improbable.

First of all, they can't immobilize a mountain; the kage's maybe, these guys no. Their proficiency underground is also questionable; we've only seen it applied for sneaking, never for fighting. Secondly, we've already got enough evidence to suggest that sneaking isn't that usable against uchiha's since they can see chackra. Against Madara they might as well run yelling.

Once it can't walk or run, they can start destroying the legs before working their way up the body.

You're played too many silly MMOs IMO. You can't just tickle it to death. If this thing could actually be destroyed don't you think the all mighty sage would have done so instead of hiding it's body up in the sky. Let's not forget that 8-tail and 9-tail are suppose to be the size of a small village, yet this thing is 100 times bigger? Their longest blades won't even make it 1/10th the way though the skin, let alone do damage to it. And even if say it was damaged, how long would it take for it to fully regenerate, with it having infinite chakra and all.

And if you're thinking about explosives, think about how effective the combined force of Naruto & Bee has been so far; and how Madara commented there's no need to even dodge or parry the shots.

I do not dispute that Naruto needed extra forces to fight the Terrible Trio, rather I question the logic of using so many soldiers in a field that doesn't require such a number (and honestly is more likely a hindrance).

In the earlier fight with Madara (the meteor one), while Naruto cared, he didn't care enough to let it get in the way; if anything he tried harder, and the forces there helped keep his clone up and kicking for as much as possible. So the only risk of being a hidrence is from his buddies. Therefore, if we're thinking about eliminating hindrances, it's not that only his friends should be there, but rather, anyone but his friends should be there. However, his friends are probably the best the entire ninja army has to offer (with the kaje's now indisposed), so them becoming hostages and such is just a risk they have to take, if they want to have a chance to win. Never gonna win a war if you're not afraid to break some eggs.

I'm not saying there's not going to be energy wasted in "saving the army's sorry ass", but it's a case of the situation, unfavorable as it may be, still being way better then Naruto and Bee fighting it alone; especially now they're in recharge mode.