I think you're right that we'll need help, but honestly considering we don't know who's going on the mission and who will make it back, any specific advice might be pointless. Assuming Jiraiya needs time to prepare for the trip and handle things that aren't us, he probably won't be able to walk us through a list of possibilities. Without knowledge of the future, it seems kinda pointless.
I think as long as Jiraiya, Shikaku, and Tsunade don't all die, we'll have someone to give us some guidance... even if Shikaku will likely be guiding us toward his own agenda.
Though maybe it couldn't hurt to get some general advice. Like asking which clans outside of Ino-Shika-Cho can we trust to at least deal with us in good faith. I think if we don't try our hands at diplomacy outside of those 3 clans we risk becoming Shikaku's pawn... which might not be a terrible thing, but would limit our agency.