Animations
He can look into OpenToonz (used to be called something else, used by some anime creators and about 2 months ago the software went open source, so it's free to use), but animation is not simple or fast. If you are going to be drawing frame by frame (even if you can copy the majority of the previous frame) it will take very long. I don't know if it has built in animation tweens and stuff like Flash has.
On the paid (I know, you asked for free.. but whatever, I want to give you an idea of what exists) Adobe side of things you have Flash and Animate. Flash has been used for years now and you probably have at least heard of it. Can't say too much about it that you shouldn't already know. I believe The Simpsons is done in Flash now
Animate is a slightly newer program of Adobe, but I heard it's like Flash.. But less stable and overall not better.
You also have GoAnimate, which I believe is used in all the Seth McFarlane shows (Family Guy, American Dad, etc.), but I don't know too much about it.

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