I tend to get my toon or my toon's son married as quick as possible after they are 16 years old. Then my toon's son will give born to his son before he is 20. Now the problem is, when my toon die, my son is already 3x and his son already pass 16 or even 20. Therefore, i dont have the chance to educate him. If i need to have my son's son educated. What i can do is delay the marriage of my son, but it is unreasonable because in history, people at that time were married very early.
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If your heir holds a landed title, he should get the events to educate his own son. Otherwise I would like to see your heir without a landed title having his heir educated by choices the grandfather (your character) makes. I suppose this could be tied to the listed liege.