1. Entries in one month's CSV file may be repeated in the previous or following month's CSV file, typically movements at the beginning or end of the month that the bank takes some time to record, or adjusts later. Is this familiar with you and how do you address it? Is your system robust against it?
2. Credit card: the total amount for a month is one single entry in the bank's CSV file, while a separate CSV file contains all the details. Do you rely on accounts to handle this indirect flow, e.g. one transaction of 1000$ from checking to cc, based on the single entry of the bank's CSV, then several transactions from cc to the various expense categories, based on the details CSV, and checking that the cc account has a zero balance?
3. Some utility companies bill every 2 or 3 months. This makes monthly stats meaningless (why is September so high compared to August? did I spent too much or is it the effect of the phone bill of the previous quarter?). Do you make any effort at trying to allocate such expenses to the month(s) when the cost originated, rather when it's billed?