I just got bit again by a MoneyDance annoyance which is once you change a date when entering a transaction, that date sticks until you change it again. If the next transaction is a check you want to print, you can inadvertently print a post-dated check - sometimes a few weeks in the future (happens after I post a scheduled future payment from the checking account).

Quicken, when I used it before MD, would not print post-dated checks unless you jumped through an extra hoop. Something similar or a warning that it is about to print a post-dated check would be very helpful. Right now, I have an upset contractor thanks to inadvertently giving him a check his bank refused to accept.