Ok, thank you for expanding, I think I've found our disconnect.
I think there is a pretty good chance(on the order of ~50%) that Oro is doing his own version of the "yoink" plan, and does not plan to cooperate with Leaf. If this is the case, I think that cooperating with him will go extremely badly.
I'd like to try to establish what Oro's plan is before we meet up with him.
I would rather make contact with Naruto through the Jiraiya's ninja contact in Otofuka Gai. Once we've been briefed by Naruto and have more info about why Oro went missing, we can decide if we want to contact Oro again via the 7th path.
Alternately, I would rather head to the EN and kidnap a random leaf-nin or info broker, and pump them for info on why Oro went missing. If he was under Akatsuki pressure(directly or by leaning on the Kage), we conclude he's probably planning "Return to Leaf" and rejoin him. Otherwise, we conclude he's planning "Oro!Yoink" and don't meet up with him.
Even just sending Oro a toadmessage of "Heard you went missing, what's up with that? will you be able to get support from Leaf?*" Would clarify the situation immensely.
*"Also, please treat Gamahebigai respectfully, and with as much comfort as this communication channel allows. We'll summon him every few hours to check messages"
Do you think we're on the same page now with regards to what eachothers positions are?