Managing Shinkansen and other train tickets for August travel

I‘m traveling to Japan for three weeks in August and besides booking hotels I‘m also thinking about getting train tickets early if necessary. My rough travel plan is Tokyo – Kyoto – Osaka – Hiroshima – Tokyo.
I have decided against the JRL-Pass but am strongly considering using one or two regional passes.
If I understand everything correctly, I do need to reserve tickets for trains nonetheless.
So my question is twofold:
How do you reserve tickets for the timeframe your using a regional pass and otherwise?
Is it necessary to book every trainride well in advance?
Does this only regard Shinkansen trains or should I prebook all my trains?

Thanks in advance for your help!

by Semi8

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