While I can appreciate the general concept of designing withing limitations, 1.44MB just isn't quite the limit it's being presented as. Look at Pico-8 games, for example. With the full Pico-8 runtime environment bundled in, typical games still clock in well under 1MB for Windows builds, and even smaller for Linux (macOS builds bloat up to 3+ MB, unfortunately). That's an entire virtual console + a full game, and still half a meg to spare on a floppy.

POOM, the DOOM clone, is a "multi-cart" on the Pico-8 and still only comes in at 1.2MB on Windows. I guess what I'm getting at is, if someone wants a fast-track to meeting the challenge of 1.44MB, make a Pico-8 game.