I may be the real minority here: I eyeball the credit card bills every month when they come in, make sure we don't have anything stupid or anything fraudulent, and pay them. I eyeball our bank account statements monthly for anything fraudulent, but there's never any expenditure except for our regular monthly bills. That's it. We just don't buy stuff we weren't planning on.
You and me buddy!
Wife and I watch the dollars closely as they go out - I audit payroll, CC, and bank statement every month - and let it go. Tracking the individual expenses seems like a waste of time unless it's just for curiosity or trying to convince a family member to change habits.
I catch an error every couple months. Just recently a $50/pay period medical surcharge on payroll which was in error.
Watch the Washingtons, and the Benjamins take care of themselves!!
I have this debate with my wife all the time! I am fairly obsessive about entering everything in to Quicken. She rolls her eyes whenever she sees me entering the information. However, she is always impressed when I can quote her exactly how much we've spent on groceries, child care, gas, vacation, etc during any given block of time.
I think the value of tracking expenses depends on your desire to manage your finances and how complex their finances are.
I started tracking when I was deep in debt, probably almost 20 years ago. I was in a situation where I should have had a positive cash flow, but never did, and I had no idea where the money was going. It was such a revelation when I tracked all my spending that it has just become a habit now. I would say that tracking is about 10x easier nowadays in Quicken since there is very minimal manual entry. The downloading feature is very handy, and it works well once you figure out the quirks.
Currently, I track all of our transactions. We have accounts at several banks, brokerages, credit unions, retirement plans. We frequently move money between accounts. The main advantage of tracking is that it gives you an accurate picture of income/expenses and you can reasonably extrapolate everything into the future as you are nearing FIRE status. Quicken itself has a great retirement planner, and moreover, using FIREcalc or similar calculators, the output is more reliable than if you ballpark the inputs. Remember "garbage-in, garbage-out."
Whenever we wonder if we can retire early, I can just show my wife the data and state with reasonable confidence whether we can or cannot. Also, I can model a bunch of what-if scenarios.
I think if we were younger, this wouldn't concern us that much, but as we get closer to retirement, I believe that by keeping such detailed history, it has been valuable in terms of planning our future.