Tested Blender's Eevee, Rigify and Dynamic Paint with a Bob Ross inspired scene. In the end, the rig worked awesomely (with good default skinning), but I went and created some unnecessarily complicated extra rig constraints to animate the brush. The animation is really sloppyish but I wanted to get this done in one day. Took a bite too big to chew in a way. :P
I color-graded the sequence and added the music credits and motion blur with Adobe After Effects.
Music from https://filmmusic.io:
"Smooth Lovin" by Kevin MacLeod (https://incompetech.com)
Licence: CC BY (http://creativecommons.org/licenses/b...)