The question to ask when tracking to optimize reoccurring bills for home and grocery is if there is even any room you can give anyways.

You'd probably find the easy end actionable changes better by tracking the amount and which food spoiled before eating, or by testing your standard basket item costs at different stores you are willing to go to. But all of this isn't something you need to do continuously. Once you figure it out, you should be good for some period of time.

The hard part has been to import all the accounts and to categorize the transactions on the 1-2 cards and 1-2 checking accounts that get used a lot. However doing hledger motivated me to simplify things. Either delete cards and accounts. Or barely use them so I can update them once or twice a year. And helps to reduce the number of categories.

I have not made updates for all of 2025 after 3 or 4 years of hledger. ROI diminished once the itch to zero everything wears off and since I have somewhat steady state expenses.

If ROI has diminished (maybe dopamine diminished?) then what keeps you motivated?

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.

have a "Costco purchases" sub-category for "groceries". If you ever feel differently, just move it to "home". Your system has to support this though. I did multiple re-organisations in the last 10+ years.

Maybe the right way to do this is to only track accounts, and no tracking of individual txns?

Importing and tracking 401k contributions and stock dividends across multiple brokerage accounts - and then trying to handle timing differences (money in flight)… oof

Yes. Also wondering about the ROI. What do you gain by this?

For transactions: you spot fraud, mischarges or subs to cancel. Really a watchdog service would be good here. High effort, low return. IMO. (And a bit of tracking around reimbursements)

For savings: helps you keep an eye on where you’re at by forcing you to reconcile.

It’s totally worth it for a low value of invested time. But, it’s not going to be low effort.

So sounds like the ROI is not really there?!