I assume it's these two question you've referring to:
While the first one can be seen with some good will as retro by being a 16 bit COM program, it's still a generic debug my program question; the second in turn completely leaves this territory by being a high level, machine independent algorithm coded in C. It's pure CS theory and as far from retro as it gets.
I would agree that the core component of this question is already covered in several answers to the question: Are x86 Programming Questions on Topic. Maybe a bit indirect. So it may help to point it out more directly:
RC.SE is not a debugging service.
The very same way as RC.SE is not a homework service.
There will always be a class of questions where the core is hard tied to a classic hardware, software or combination thereof. And those are not only fine, but very welcome. So we need to filter and protect them.
I do not think that size or language does really make a point for on/off-topicness. What does is how the problem approached and presented: I would expect the problem being analysed and broken down to a level that excludes generic CS and obvious debugging issues and presents a state the one asking can not explain, because the asked for component is not obvious using today's common knowledge (*1).
Using such a common sense classification could easy rule out all four of the questions mentioned. Fair rules/judgement are rarely about form or size but need o look at content and meaning.
*1 - This also means showing basic research, like what an address on the CPU programmed is, or that Assembler really executes straight ahead ...