I use ledger myself, but the issue I always run into is my wife is much less likely to keep track of what she buys and let me know so I can record it. Where that gets especially tricky is when she goes someplace and leaves a tip. Resolving tips is a real pain in the butt, especially since it comes through in the checking account at the original price and is then later processed at the tip-included price. Matching those up is a real bear.
I also had a similar issue, but then it became like a habit – every night I would check my accounts and add day's expenses (it's difficult if you have a lot of cash transactions). For the tip, wouldn't you round off to nearest full digit? You can just add that as an expense.
I used to reconcile our purchases against our online checking account every night, but the issue with tips happened when I would do that but then a few weeks later I would go through and actually balance everything out and suddenly I'd be off by a dollar and change and have to go on a deep dive to find out where I went wrong.
