Nice, chip8 is a lot of fun. I looked at your emulator implementation too, and it looks like you have an OOB access bug in the "I" register (it can be incremented beyond the RAM array bounds). This is a very common chip8 emulator bug, which can (in some cases) be exploited to allow a malicious ROM to escape the emulator. I wrote about this here: https://www.da.vidbuchanan.co.uk/blog/bggp3.html

Awesome milestone! As someone diving into C and C++ right now, what was the steepest part of the learning curve for you when structuring the assembler compared to writing the emulator in C?

Really cool project. How much harder did the assembler feel compared to writing the emulator?

Nice job!