◇ Could this help me?
Yes, and two ideas in it are worth lifting even by someone who never builds the tool. The first is forcing a binary decision on one item at a time, which works because the cost of task lists is the scanning rather than the doing, and it is the same reason triage queues are designed that way everywhere else. The second, and the more valuable one, is recording how a task was actually accomplished after finishing it, since that record is precisely what makes handing the task over later possible, and almost nobody keeps it. General practice, with an honest note that the behavioral-nudging part is the weakest claim, because a tool that notices avoidance can become one more thing to avoid, and the metacognition framing is a hypothesis rather than a result.
Help me build a triage loop for my task list that shows me one item at a time and forces a single decision. The options should be do it now, not now, already done, waiting on something else, hand it to you, or drop it. After triage, run a timed sprint from the do-now queue. Then add the part I actually care about: when I finish something, prompt me to record briefly how I did it, and keep those records so you can take on similar tasks later. Tell me what format those records need to be in to be genuinely useful to you rather than just notes to myself, and build nothing that nags me about what I skipped until I ask for that.