Another option for RWBY working with Ironwood and sharing important information with him: They're not actually bothered by working with a dictator until that dictator is no longer on their side. Which would make them pretty vile, tbh. So it would reflect better on RWBY and co if he wasn't a dictator until the end of V7.
Exactly. Like, I've been paying attention to things like Miles Luna saying they'd originally written Ironwood to be a bit of a dick but then 'discovered he had a heart' and the writers saying that he was a 'fallen hero' and had paved the road to hell with 'good intentions' and that the ethical dilemma at the end of volume seven (rescue Atlas, the already evacuated Mantle citizens, and the Relics Salem wanted at the cost of leaving behind the remaining Mantle citizens or trap Atlas, the already evacuated Mantle citizens, and the Relics Salem wanted at the risk of losing everything on the off chance they might be able to save more people) was meant to be one with no clear answer and no clear right and wrong. The 'Ironwood was always an evil bad dictator' people should logically see that sort of thing and actively think the writers are incompetent or liars, or that they're so opposed with 'Alpha Males' that they didn't even realize they were writing a dictator, or... They're pro-dictator. Either way, it would - using their logic - reflect badly on the writers and would inevitably also make the group of heroes look really really bad in universe.
Like, the way that I see it is that the writers made Ironwood with the vague concept of maybe potentially being a bad guy later on, but using their flying by the seat their pants writing style decided that Ironwood worked better as a good guy during the Beacon arc and tbh also the Mistral arc, and then continuing with their fly by the seat of their pants writing style, decided to try to do a morally complicated plot with the whole volume seven, and then decided they wanted villain Ironwood and started making him a 'villain with a point' who was against Salem but also way too 'ends justify the means' and also needed to be stopped. And although I don't really like fallen hero arcs as a general rule, the concept itself isn't a bad one and I just think it was really poorly executed. But the way this angle of the 'Ironwood was written as a flawed good guy who did morally gray things with his back to the wall and then was suddenly written to be villainous evil for the sake of it scum' thing reflects on the characters in universe... Isn't super bad actually. Sure I think Ruby and co could've made some better choices and some of the way the writers decided to characterize them is annoying and again, badly done. But 'they were working for a good guy despite the fact that they didn't always agree with him on everything and he wasn't always perfect, they had a pretty big ideological difference of opinion that drove them apart, and then Ironwood started going absolutely off the rails bad seemingly out of nowhere, making Team RWBY and co have to take him out'... While I still think it was badly done, that reflects so much better on Team RWBY and co than the 'they were willingly and happily working for a dictator for months and the only explanation for it is incompetence or them actually not minding dictators' that comes with the 'Ironwood was always a bad evil dictator' angle.
Like, seriously, what is the angle that the anti-rwde posters think they're taking when they say that the only people who don't think Ironwood was a bad evil dictator are either stupid, pro-dictator, or misogynists who love alpha men, when TEAM RWBY AND CO didn't think he was a dictator, and the writers talk about him as a fallen hero with good intentions? If Ironwood really was a dictator, than Miles Luna and the other writers and Ruby Rose and the other heroes are in the exact same slot that I am.