These days, I find it is doable 2-3 times a year. Its a lot of work at one shot but somehow able to catch up so as to review the main spending accounts. The zeroing is what attract me still. I get to see some patterns in my overall spending/categories. And it is side project where there is perceivable concrete progress, so still somewhat easier dopamine.

Simplifying/automating the workflow is a pull. As I type this, I have an idea to stop tracking NW in hledger - it can seem incomplete because money moves from checking to brokerages. That's fine. I only want to see expenses.

Interesting! In a different comment, I took the other side: maybe it’s only worth tracking NW in hledger? Itemizing transactions is heavy duty bookkeeping effort, and I didn’t feel any directional value.