These questions are very helpful to the person asking, and great for driving activity. I think it is good to allow these questions to be asked and to answer them.
At the same time, they are not good for keeping on the site indefinitely. Many years ago, I did not understand what lambdas were and asked a bunch of very specific questions about why this and why that and wherefore syntax error in this piece of spagetti code. This was back in the good old days and people on SO actually helped me understand it. But does it matter now? Would anyone read the question? Another person with the same problem would have trivially different code. But if they are a novice, they would not be able to see past the trivial differences.
Moreover, the real value in troubleshooting is not solving the immediate issue, unless that exact issue is extremely common. The real value is a hands on lesson in learning how to fish.
It would be great if we could find a way to do that. For example, in my lambda example, perhaps the solution would be to close the specific question, and create a new one saying "how to troubleshoot syntax errors [involving lambdas?]"?
I think the Latex community at SE started a great tradition of asking for MWEs. I believe the R community later started adopting this as well. But not every problem can be easily turned into an MWE. However, every troubleshooting/debug problem should reduce to a generic problem solving case study.
So we need a way to handle these questions, but unlike others, simply answering a troubleshooting question does not actually grow the knowledge base of the site. Extracting generalized take-home lessons from the troubleshooting grows it. So the specific problem is not the issue, it's how to approach that type of problem. We need to somehow convert the troubleshooting questions into that type of generalism.
Perhaps some kind of chat function would work for this? We could encourage users to ask for debugging help in chat, and from there point them to or encourage making questions like "how do I troubleshoot errors of X class in Y context?"