I haven't recorded anything in a paper checkbook register in well over 20 years, but every check we write (probably about 50 a year) gets entered in Moneydance (the equivalent of Quicken etc.) within minutes or hours of being written.
Every month I reconcile the bank statement (downloaded as a pdf) with my Moneydance file.
Every month I reconcile the bank statement (downloaded as a pdf) with my Moneydance file.