I've been tracking my finances, with varying levels of details, since 1997. I started with Microsoft Money, and tracked everything including cash and credit ca

I've been tracking my finances, with varying levels of details, since 1997. I started with Microsoft Money, and tracked everything including cash and credit cards charges, for 10 years. It took a while to enter the info and I wasn't really using the info at that detail, so I changed up and also migrated to Moneydance, since Microsoft Money sunset in 2009. I started over with Moneydance, and instead of recording cash to such detail, I just recorded it as a transfer from checking to "Wallet - Cash" and then balanced that every month by assuming all my cash went to restaurants. Not 100% accurate but mostly correct and way faster. After a 2-3 years of Moneydance I decided to migrate again to GnuCash, for the various benefits of open source software. This time I also lightened up my recording to condense credit cards purchases down to one monthly entry. Which again saves a lot of time. I glance over my monthly bill to make sure the charges are correct but don't split out by category anymore. So that's where I am now. Been using GnuCash for the last ~10 years, only record large categories of expenses and basically check credit cards bills for accuracy and keep my checking/savings accounts up to date. I only update retirement/investment accounts once a year, at the end of the year. I am fortunate to be able to live below my means so I don't have to stress over balancing various accounts to the dollar. I just need a general idea of my position.