Okay, so, looking at the character sheet, it appears that additional training actions for a given skill are subject to diminishing returns.
Our last action had us train Ninjutsu, Genjutsu, and Kenjutsu once each; Genjutsu and Kenjutsu each increased by 7, while Genjutsu increased by 10.
Knowing this is the case, but not knowing the point where diminishing returns begins, it becomes hard to predict how precisely the training will affect Hisana.
Worth noting is that Strength went up 5XP, and Speed went up 7. This is somewhat interesting, as we only had one option that was based around physical training (Kenjutsu), so this would imply that the Kenjutsu training gave us the following XP breakdown:
Kenjutsu Training:
7 XP - Kenjutsu
7 XP - Kenjutsu Subskill - Leaf Style
7 XP - Speed
5 XP - Strength
We also gained 5 XP in Chakra Capacity, pushing us to 40 there, and 15(?!) XP in Chakra Control. We probably got 5 XP to Chakra Control from each Nin, Gen, and Iryojutsu, and 5XP to Chakra Capacity from Ninjutsu.
We also got a hell of a lot of XPin the subskills, Basic Genjutsu and Sharingan Genjutsu (20 XP each), bringing them up to match our overall Genjutsu rating.
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I think it would be better to wait on the summonings. If we have to pay for a mission to retrieve the scrolls, then we are not strong enough to use the summoning scrolls in the first place.
-edit-
Don't be blinded by the shiny.
We've got pretty decent Chakra ratings, actually. Our Chakra Capacity is 40, and our Chakra Control is 45- That is, low-mid Chunin rank in both. Further, Ninjutsu training is likely to give us more points in Chakra Capacity, pushing us up to mid or mid-high Chunin rank.
We have evidence, in the form of Temari's fight with Tayuya, that roughly Chunin-rank ninja can perform the summoning technique adequately. We probably won't be able to summon a taxi, at least not immediately, but we
should be perfectly capable of summoning scouts and such even at this point.
Anyway, going to sit out building a plan this time, since we've already got a pretty strong set of bandwagons going and I doubt I'll be able to pull a victory at this point. Might do some fanart or an Omake later, instead- Seems like a more effective way of influencing Hisana's build than trying to gain support for my plans.