Inside and outside views are different levels of description of the problem, and reasoning always happens on many levels, with analogies drawn between levels and with feedback between levels. The failure of rationality occurs with particular use of representation where you have your inbuilt overconfidence pull in the wrong direction. By shifting to a different level of description that doesn’t include the faulty parts, you restore rationality of the conclusion. In other cases, you don’t need to do that, and the success depends primarily on having sufficient information about the domain and correct estimates of similarities of the parts of the problems, on all considered levels of description.
Inside and outside views are different levels of description of the problem, and reasoning always happens on many levels, with analogies drawn between levels and with feedback between levels. The failure of rationality occurs with particular use of representation where you have your inbuilt overconfidence pull in the wrong direction. By shifting to a different level of description that doesn’t include the faulty parts, you restore rationality of the conclusion. In other cases, you don’t need to do that, and the success depends primarily on having sufficient information about the domain and correct estimates of similarities of the parts of the problems, on all considered levels of description.