I don't feel like waiting anymore for judges so I'll just go ahead and post my opener.
At the beggining of the battle, Jiraiya can instruct Fukusaku or Shima to summon the three boss toads Gamabunta, Gamaken, and Gamahiro for support.
You must be registered for see links
Alternatively, he can summon one himself at the beginning and continually summon several more throughout the battle. The purpose of these boss toads is to increase the number of targets Gaara must focus on and gives him the option to perform attacks in conjunction with these toads as well as creating diversions. By standing atop one of these toads, Jiraiya can cross far greater distances by instructing the toad to
You must be registered for see links
, and can also work in combination with the toad by splitting the division of labor and letting the toad concentrate on defense and evading Gaara's attacks, while Jiraiya and the toad Sages, or other boss toads, focus on offensive tactics.
Defending against Gaara's Sand assaults
Gaara's initial strategy will be to crush Jiraiya in a sand coffin, or kill him by overwhelming him with sand. The toad which Jiraiya is standing atop (let's say Gamabunta) can jump to avoid the attacks or power through them. There are several methods which Jiraiya and his toads will employ to defend against Gaara's attacks.
Either Jiraiya or Gamabunta can spit oil out from their mouths
You must be registered for see links
You must be registered for see links
to render the sand surrounding them useless and cause it to break down.
You must be registered for see links
. When sand comes into contact with oil, the slick liquid
You must be registered for see links
the sand structure, the oil causing the individual grains to stick together and solidify, which form loose crumbly rocks.
You must be registered for see images
I have heard the premise before that Jiraiya's toad oil will not affect Gaara's sand the same way as the 2nd Mizukage's oil, and that Gengetsu's oil was a special kind which was composed of both water and oil, since it was identified as "watery oil" by a member of the shinobi alliance. However this premise is false on two counts.
1. The Mizukage himself referred to the liquid as oil
You must be registered for see links
2. Oil and water cannot mix, so the idea that only "watery oil" affecting sand is false
So Jiraiya's toad oil should have the same or at least similar effect on Gaara's sand as the Second Mizukage's oil, which breaks down and disables sand at a rate fast enough for the Mizukage to quickly make it through a large pyramid of sand
You must be registered for see links
. At the absolute worst, Gamabunta's
You must be registered for see links
or Gamakichi's
You must be registered for see links
used in conjunction with Jiraiya's oil which would destroy the sand and eat through it. Should a wave of sand come sweeping down in front of Gamabunta, he can spit a mass of oil at the sand to weaken it, then bust through it with his incredible strength. If Gaara attacks him with sand arms, the toad can easily cut through the sand with his weapon
You must be registered for see links
. The toad's sheer size alone is an advantage, as it takes more sand to restrain a boss-sized summon like Gamabunta, and therefore it takes more time and effort for Gaara to move a large mass of sand in formation than it does to move smaller amounts, which can quickly snag opponents.
Gaara's sand also has trouble keeping up with opponents. Joki Boy was easily dodging Gaara's sand
You must be registered for see links
You must be registered for see links
, and Deidara's clay birds easily outsped his sand
You must be registered for see links
You must be registered for see links
. Even Deidara on foot managed to jump out of its way at close range
You must be registered for see links
. Lee was far too fast for Gaara's sand to keep up as well, despite the Shukaku automatically protecting Gaara with his sand
You must be registered for see links
. Toad summons which can cross large distances and are very fast can outspeed his sand, except for the Ultimate Defense which can be guarded against and repelled/disabled/powered through, should Gaara decide to use it offensively.
Escaping Sand Coffins, should the need arise
Though unlikely, Jiraiya may be in a tight situation where he won't be able to avoid sand coffins by normal means. To avoid getting crushed, Jiraiya can employ any one of a number of strategies.
1. Summon a toad to disperse the sand
You must be registered for see links
You must be registered for see links
.
2. Repel the sand with his strength
You must be registered for see links
You must be registered for see links
. Jiraiya has shown to have tremendous strength when in Sage Mode, capable of
You must be registered for see links
with his sheer strength. Remember Jiraiya underwent the same training Naruto did, and Sage Mode grants him
You must be registered for see links
3. Spit oil from his mouth to disable the surrounding sand.
4. Tank the attack with
You must be registered for see links
.He can manipulate the shape of his hair into different forms
You must be registered for see links
and can enlarge and expand the size of his hair
You must be registered for see links
to surround himself and protect himself with a thick, hard shield of hair. That being said, his hair has the strength and durability to
You must be registered for see links
so it should be able to withstand the pressure of at least one sand coffin, considering Kimimaro was
You must be registered for see links
with his bone armour prior to even activating CM2. Gaara's sand in Part II also has not shown the feats to crush anything of noteworthy durability, a testament to this being that he needed Onoki to destroy the Mizukage's clam rather than crushing it with a sand coffin.
On the offensive
As I mentioned earlier, the toad which Jiraiya would be standing atop would be focusing on the defensive, whereas Jiraiya, the toad sages, and other summons can concentrate on attacks. Now, Gaara will likely assume his strongest defensive position surrounded by his Ultimate Defense with his Third Eye keeping a lookout.
You must be registered for see images
What Jiraiya has to do is close any distance between them and breach the sand shield. Closing the distance won't prove to be difficult, due to the leaping power of his toads, which allow them to cross huge distances. Gamakichi was able to cross dozens/hundreds of juubi clones with a single leap; Gamabunta easily crossed
You must be registered for see links
distance in one jump.
Upon closing the gap between them, Jiraiya or a toad can douse Gaara's protective layer of sand with oil, then ignite the sand on fire with a katon, roasting Gaara with
You must be registered for see links
or
You must be registered for see links
. Or, Gamabunta can rapid-fire
You must be registered for see links
to tear through the defense and kill Gaara. If a boss toad manages to leap above Gaara (not necessarily the toad which Jiraiya is standing on), its weight will crush Gaara - or if Jiraiya gets above him, he can summon a toad on top of him and crush him with Food Cart Destroyer. Fukusaku or Shima can use their tongues to wrap around Gaara's sand "eggshell" and
You must be registered for see links
who busts through the defense and kills Gaara with a
You must be registered for see links
. Fukusaku can perhaps slice through the Ultimate defense and cut Gaara in half with his tongue since it can
You must be registered for see links
If all else fails, Jiraiya can just stall for time while Fukusaku and Shima prepare Toad Confrontation Chant which paralyzes Gaara upon him hearing it, and with Gaara immobilized he will not be able to control his sand. This leaves Gaara vulnerable and makes him an easy picking for Jiraiya, who finishes him with an Oodama Rasengan.
Jiraiya takes this med difficulty due to his boss toads, versatility, and powerful attacks.