1-. Ranks Gives you Mana which you can use to level up later. The higher more mana you get. S and SS give you useful Permanent Will that you would normally get on the next chapter and even later.
2-. There is no better time to level up. When the a Trainer character gets a Level Increase in it's Reinforce skill you should just level up all you character as much as you can.
3-. Just give the PW to someone with the most useful skill. That's what I do.
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