I think you're right and that there should be some pain. My version of this is taking a full list of transactions and tagging them individually from electronic exports. This way any expense isn't reconciled until it's tagged. This can be done mostly automatically but some are unrecognized/unique expenses. The unrecognized are the ones that probably matter the most in terms of managing my finances, dinning out, random items from amazon, etc. I have to review and recognize everything which makes me monitor the most important aspects where I might have spent my money poorly.