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I don't think there is a difference how calibre converts. The only scenario where kindle to epub would be worth would be if the kindle book is only an old mobi.
Reading comics is definitely better on a tablet. Since he is 8, a 6" reader would be easier to hold for him. Since you know how to use calibre, I would say either kindle or kobo would be fine. I don't know if and how good this is integrated in the kindle, but amazon also has a family sharing option (so he can read books you buyed at amazon) and free time (which allows you to manage which books he can read).
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