[berkut]

I've tried a lot in the past as well, and after getting annoyed with proprietary OS X software (iBank in particular) back in 2009 or so, and not really liking GNUCash and KDEMoney (at least back in 2009) ended up writing my own open source simple app (native Cocoa, with a more recent Qt port for Linux) that I've been using every since on a daily basis.

In terms of the detail, I used to do very detailed breakdowns of categories, but now I don't really see the point: my app supports 'split transactions' (one of the reasons I actually made it, as existing solutions had poor support for them back in 2009), and I generally just use things like 'Food', 'Drinks', 'Essentials' as categories, as it never really made sense (at least for me) to detail them with such accuracy.

But for things like 'coffee', I do 'Drinks:Coffee', so I can see how much I am spending on fairly specific things, but I guess it's a balance in terms of whether it's worth the effort to record them so accurately compared to making use of the details.

Similarly, things like 'Car:Fuel', 'Car:Service', etc...

[tunesmith]

At some point I really should do a first principles analysis of why I track money... as far as I know, it mostly comes down to: 1. is fraud happening? and 2. Am I saving enough for retirement? Oh, and I guess 3. taxes

For fraud, I think it's basically a matter of whether we can recognize each transaction. You don't actually need to download transactions for that; you can just skim your monthly statements.

For saving, that's tricky because there needs to be that recognition of what categories are likely to increase during retirement versus decrease. I gave that a single pass a while back, and now I have a count each month of those expense categories that will continue into retirement, along with a 12-month average, so I can get a sense of what my portfolio needs to be able to fund after I retire. For that, even though I have Banktivity, I also have to use a spreadsheet.

For taxes, I don't know if anything really makes that easy. It's hard to know what category breakdown you really need to know whether you're capturing all your tax benefit, and my financial software doesn't tell me "oh, by the way, you'll want to split that transaction since some of it has a tax benefit."

[hippich]

In the early period after moving to the USA, for a few years I was tracking money in and out in great detail. Including splitting checks from stores. And while I did not set explicit budget, I believe it allowed me to keep our finances healthy. And it certainly decreased money-related anxieties, giving me sense of control.

I stopped doing it after a few years, after I felt pretty secure financially. And that certainly coincided with more spending on things that I would otherwise not spend on...

[dogline]

Your grandparents tracked money because they were also verifying the math, which could have done by hand. Now, we assume the math is right, and we're checking for fraud.

That, and we like to watch a number go up.