Re: #3 In my own software, I always enter the initial date (or date I expect it to post) and then I don't worry TOO much about it unless say it's right at the end of the month. Because when I view reports, I want the month-end balance to match my real accounts. (For this reason, I also tend to avoid doing things like paying credit cards on the last day of the month, or transferring money between accounts in such a way that the effective debit is a different month than the credit!)