"Are we trying to save money? I don't mind either."

"Staying out of town would allow us to conceal the pattern of our movements more effectively."

"Yeah, that too. Might be reasonable in a bigger city to stay somewhere there'll be rumors? But no need here."

"A camp it is. You three go ahead and set up; I'll pick up some supplies."

"Alright! We'll pick a site then."

There is a sheltered spot a little ways off the road north of town that would be suitable.

That seems good!

(Naruto's clones make setting up camp very time-efficient.)

This benefit of working with him is not unappreciated.

And he's very appreciative of working with people as organized as Chihiro and Sasuke!

Jiraiya returns with supplies, and they can cook and eat dinner.

The next day is spent traveling, and the day after they reach the first big city.

Exciting! Is their plan for this similar to last time?

With one difference: they'll be using the buddy system.

... Probably Naruto should partner with Jiraiya since his plan had been 'turn into an adult and join some gambling tables' and neither of his teammates are infiltration types.

That sounds like a fine plan.

(And saves Jiraiya from suggesting it himself. He got a message that Akatsuki is on the move.)

"The name I was using last time was Aji. Though I can do guy or girl?"

"Whichever you feel more comfortable with. It doesn't matter to me."

And: girl Naruto!

"I think this is a pretty good face for it?" she says. "I look young enough to be gullible."

"A good disguise," Jiraiya agrees. "You have a talent."

And it's off to the gambling halls for them.

"Thanks."

Gambling! (What's their basic cover story, old man, or should she start making up shit like 'oh yeah, my grandfather...')

Grandfather is kind of... Jiraiya shudders. Makes him sound old. How about uncle?

Sure. He can be her pervy uncle.

That's also a little... eh. Good enough.

The gambling halls are much bigger than the bar. There are two halves: cards and dice. The cards attract more serious players, for bigger pots, but the dice move more quickly.

She's fairly new to gambling! She's gotten an introduction to poker, doesn't really know dice rules...

Cards seem more likely to have what they're looking for, though.

Jiraiya puts up a stake for a seat at one of the card tables. His 'niece' can kibitz over his shoulder, and perhaps gossip with the other onlookers.

She'll do a bit of both! And observe the flow of the card game.