They plot out their route and specific locations of interest in a bit more detail before retiring for the evening.

The next morning dawns cloudy, and threatening rain.

Aw. Well, they packed clothes good for different weather conditions, at least.

Onwards!

The promised downpour arrives about midmorning. Chihiro flicks the hood of her raincoat up without comment.

Jiraiya carries on as though it were a fine sunny day, singing a song about honey wine and drunken bears.

Yeah Chihiro's teammates are also raising their rain hoods.

"Can you maybe tell me some stuff about Tsunade?" Naruto asks Jiraiya between verses.

"...and they buzzUZZuzz!- Oh, like what?"

"Personality stuff, why'd she leave Konoha, would anyone be with her, what's her opinion on the Hokage position last you heard... Kind of just stuff for when we're trying to convince her to come back?"

"Hmm. Well, Tsunade's... Tsunade... She's sweet, but she's got a temper." Jiraiya tells a few stories about getting on the wrong end of that temper, back when they were genin studying under the Third Hokage.

He listens intently, trying to figure out if there's common threads to what annoys her.

Based on the stories told, it's whenever Jiraiya interacts with her in any way. (One must remember to consider the source. She doesn't seem to have much use for fools or people looking down on her or wasting her time.)

Yeah that makes sense.

Does he have stories about her interacting with other people?

Jiraiya tends to make himself the main character in any story he tells.

(He does talk about Nawaki and Dan. He looks up into the rain perhaps more often than is necessary while so doing.)

He... Might have to think really hard at how to navigate around their memory.

Jiraiya has no hints, there.

Honestly interacting with people directly's best for that kind of sense...

This is true.

They make camp that night in a small clearing off the road. The next day, they reach their first destination, a medium-sized town.

Chihiro will scout the market.

Let's see, if he was going to be complaining or telling tales about a possibly drunk famous gambler and her short temper, where would he go...

He's guessing this place probably doesn't have an actual gambling hall, being medium-sized, but does it have like a bar that people could maybe play poker at?

Sugira, meanwhile, figures there's a fairly decent chance Tsunade has at least one item Jiraiya could describe in sufficient detail for a targeted divination.

He finds a bar, trying to pick out one likely to have people trading rumors, gets something to drink and snack on, and sits off to the side, keeping his ears open but mostly working on reconstructing a locate spell. He's modified the way he takes notes enough that he can make it look like he's bored and doing math puzzles.

Gamblers are unwilling to let a twelve-year-old sit at their table, even or perhaps especially one with a Konoha forehead protector.

Most of the rumors concern Sand's recent attack on the Leaf. It doesn't seem like it's going to blow up into another war, but it's early days yet. Cloud's always watching for weakness.

Okay that's probably reasonable. 

(...Anyone who looks like they'd notice a transformation? Naruto's good at those.)

If he did it right in front of them, probably. Otherwise it's doubtful.

Then Naruto wanders off for a while, hangs out in the market, and heads out of anyone's sight to turn into a girl. An adult girl, even.

She heads into a different bar than the one she tried in as Naruto, smiling a bit shyly, and introduces herself as Aji, and she's a bit new to all this but her boyfriend had someone he was meeting, so she thought maybe she could watch some games, learn a bit, while she's passing the time?

Oh, of course. She's more than welcome.

Learning to gamble! (And gossip! About gambling. And gamblers. And fun matches...)

(Mostly she's looking here to learn how to fit in to a gambling hall when they get somewhere bigger, but she won't change the subject if someone starts talking about the Legendary Sucker.)

No one who matches Tsunade's description is mentioned, but the table is pretty low-stakes. There's not much more than what she'd make for a C-rank in the pot.