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The running list of expenses is actually something that they've implemented recently on the Pathfinder side (if I remember correctly). They might be able to do something similar for purchases in Shadowrun.
Personally, I use the Journal to keep track of Session information, particularly since you can add notes and things to each entry. Generally, I don't use HeroLab to keep track of my day-to-day purchases and I usually calculate gear costs separately anyway, so I mostly just factor that in when I input the data for the Session.
I definitely agree that keeping track of what happened to your money and when is important, sometimes things might trigger a cost accidentally, or if you add gear and need to make corrections it does some wacky things sometimes. Without a history on the money it can be hard to tell if something happened that led to some sort of mistake...
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