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Hmm, for example, regardless of the castle, I always max out logistics (because I'm playing for myself!) and higher education. After that, it's much easier to level up! Any school of magic + attack/defense, and the hero is ready! You can also take luck if you have enough skill slots.
I never level up leadership as a primary skill for my main hero. I create a second (third, fifth - it doesn't matter) hero for that.