I can not give you an answer, but a few tips:
Big Guys do such work in a system with special hardware that allows the processor to be single-cycle, check registers, etc. And they can do most of the work on an emulator that has the same objects. Installing a hardware debugger is probably beyond your ability to create (and a little more expensive to buy), but the emulator is quite feasible (and how Gates and Allen started working on Altair BASIC - if Allen hadn't written the Gates emulator still play video games at Harvard) .
With the exception of the full debugger, if you have any type of character mapping, you can embed instructions in debugged code to write characters to the display as the code moves. Path A can write βAβ in the next place (the index is stored somewhere in the reserved memory word), while path B will write βBβ, etc. Very rude, but sometimes enough to make do for small projects.
So, I would prefer to write an emulator first. This is a good way to get to know the processor.
(Regarding the integration of things, I always just say "Hey Jeremy! Integrate this for me, right?")
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