I'm trying to figure out how to animate digitally painted animations and don't know where to start with the workflow. As reference I'm thinking of Michel Gondry's style (specifically the titles here Dave Chappelle - Block Party FULL HQ - YouTube) I know he uses film but I've seen it done with older versions of flash.
If you mean this:
Then this is just a combination of camera tracking, tracking, roto and text animations. Not simple. There is slight camera movement to the shot must be first stabilized, then you need to do roto work to separate the actor from the background, then you need to add the animated text using a separate layer for each animated line of text, then layer the comp so that the original footage is on the background, the first part of the animated text as it starts to come out of the megaphone is above the rotoscoped actor, the second part of the animated text is behind the rotoscoped actor and then you need to put back the camera movement and copy the camera movement to the text layers. You will also need to track the movement of the megaphone so that you can attach the start point of the animated text to the megaphone or do that positioning by hand. AE's text animators give you the option to animate text on a path.
From what it sounds like you are not familiar with text animators so I'd start there. Check out the help files by typing animate text in the Search Help field at the top right corner of the app. Then study up on rotoscope and rotobursh by doing the same thing. Then study up on track mattes and start building your project. If there is camera movement then you'll have to study up on that too. If I were teaching this composite in a weekend boot camp we would run down the topics as I outlined them