Thanks for sharing your take on this. I've been enamored by old Hypercard games and 1bit art of the old Mac era (Cosmic Osmo especially), but I'm not thrilled by the thought of using MacPaint for everything.
If you do find a smoother workflow for 1bit art I bet the future Playdate game makers (hopefully myself included) would be overjoyed to hear it.
Whilst the single level Undo is definitely a thing (Photoshop didn’t get it until v5!) paint apps on Macintosh got much, much better than MacPaint over the course of the 1990s. The one I use, Deneba artWORKS, allows mixing vector and pixels, has layers, dither fills, and more: https://blog.gingerbeardman.com/2021/07/30/playdate-1-bit-illustration-postmortem/
I also helped Lucas out with my solution to running Macintosh on iPad. You can read about that here: https://blog.gingerbeardman.com/2021/04/17/turning-an-ipad-pro-into-the-ultimate-classic-macintosh/