Good question! In fact the ancients did something similar as well, and assembled multiple biographies of the Buddha, which included a range of teachings in more-or-less chronological order.
The first steps towards this are, in fact, found in the canon, especially in the long texts of the Buddha’s first days after awakening (Kd 1 Pabbajja Khandhaka AKA Catusparisat Sutra) and his final journeys (DN 16 Mahāparinibbāna Sutta).
The commentaries include various information about how to arrange the teachings chronologically; this information was used in Nyanamoli’s book.
As the Buddha’s biographies evolved, filling our and expanding these origins, they began to include much later material: Jatakas, more legends of the Buddha’s life, and so on. Over time, the legendary material overwhelmed the historical, and it became difficult to discern which was which.
There are indications of a critical attitude taken towards this material at some points, but on the whole, it seems that the traditions mostly accepted the legends as fact.
This lasted until the modern era, when text-critical methods, originally developed from Bible studies, were applied to Buddhist texts. One of the key innovations was archeology. At last we were able to see that Vesali and Savathi and the Deer Park are not just places mentioned in scripture, but are real geographical locations. Together with a range of critical methods, including comparative study, this gave us a much clearer picture of the historical relationship between different Buddhist texts.