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.

my thinking is that NW does not have to be tracked in a way that the double entries zero out. Every six months, I just open the 3-4 brokerages and banks and make an entry in a spreadsheet for cash/stock/bonds/crypto/others. Where the stocks are mostly ETFs and crypto is less than 5%.

And create a pivot table for totals and %s. And rebalance as needed. This may be too crude for some. But I am only starting to get organized, so this works, esp as you said for directional. Actually this is one of the reasons I have dropped hledger in general.

I just leave notes and comments in the spreadsheet as needed.