I used to reconcile my checking account monthly. Now, I just balance my account after every transaction (written check, ATM or debit card purchase) and check with the bank online the next day. So far, after several years, the bank has $23.77 more than I show in my register each month. Don't know why but it is like this every month. Like Deborahmichelle, I work from my balance so I feel as if I have a cushion. I track each check or debit card purchase that goes out and check online when I have a deposit (automatic or in person). I have lots of auto deductions each month but watch my account closely.
So I don't reconcile my account every month but I would never have a $2000+ problem as I keep track of all my spending in my account each day.
I am treasurer of one a nonprofit organization and I do reconcile the statment/account to the PENNY each month. I get a strange pleasure out of having it balance/reconcile to the penny. And if it doesn't, I spend the time to go back and figure out why. The accountant loves me. :)