Seeking suggestion on strategies on entering historical financial ledgers

I have my grandfather's financial ledgers from 1919 to 1954.  He was a farmer who was impacted by the depression, but made it through and was eventually quick successful.  My goal is to enter them into Quicken so I can answer random questions, such as "How much did they spend on food?"  And, "How did the depression impact their spending?"

I am wondering if anyone else has done this and has suggestions on categories for entering data.  I have entered one years worth of data and already see various ways to code this information.  For example, there is regular- routine farm labor (he was a farmer) and then there is specific farm labor for shucking corn.

Has anyone done something similar?