Well, just because Jirou tries to do the Otokage's plan, doesn't mean he'll succeed, or that it won't be without complication, or that the result of his success won't lead to something more troublesome.

after all, we don't know what this Masuku's girl deal is, what they're involved in and how it will affect things, we don't know the Masuku clan in general will take it, things like that there is room for this plan to just lead to whole a bunch of different unforeseen problems. I don't want the characters to be made more stupid for the sake of plot when we could have them make the seemingly smartest decision and figure out ways for those decisions to still have unexpected problems and consequences as a result, or for those plans to not always succeed, because the smartest plan doesn't always work out, Jirou could simply be unable to find a Masuku girlfriend simply because they see no reason to go through with it or give him the time of day, because a guy suddenly taking an interest in trying to date Masuku women specifically is kind of creepy or something.

like there are multiple failure points here:
Jirou might not find a Masuku girlfriend
Jirou might not succeed in taking clan head from Mitsuko
Jirou might do everything right....but still teach Kimiko the wrong lesson by example as a result

and thats just three off the top of my head. there are degrees of success and failure here and I just have to figure out how MUCH Jirou succeeds and what parts for him to succeed at. and of course, what success means really if he does. because if he does, he'll be at least taking on the responsibility of a clan head which might mean how he interacts with Kimiko might change anyways, just in a different way. and who knows how this hypothetical Masuku girlfriend will affect things? don't assume the person he gets will be some beneficial or purely beneficial just because.

My goal right now is to basically figure out how to set up as many ticking time bombs as possible, so that further down the line they explode at some point and cause even more drama. Sort of like setting up dominoes and waiting for the time that the first one gets pushed. and sometimes, the worst things can come from the best decisions. people like to think otherwise, but good things can come from bad, and bad things can come from good things, some of the time.

just gotta figure out the details, cause the devil....is always in them.