You have to be a "personal accounting hobbyist" to really make your ledger match up with reality. If you have even moderately complex finances, you will have to

You have to be a "personal accounting hobbyist" to really make your ledger match up with reality. If you have even moderately complex finances, you will have to take input from several different sources, do a lot of preening of transactions that were imported a bit incorrectly, reconcile against external sources of truth like bank statements, and in general spend time keeping your accounts straight. How much time you need to spend to do a good job can vary widely. It depends on your data sources, your tolerance for error, and how well your use cases match up with your software's assumptions. Balance that cost against the benefits, which are subjective -- how much do you value easier tax preparation? How much do you value peace of mind from having your financial state clearly articulated? How much do you value understanding your in and outflows, making a budget, monitoring activity for potential fraud?