I'm no stranger to personal finance software. Hell — I've written about most of my experiences with them here on this blog. Moneydance, Mvelopes, Wesabe, and most recently, Mint, all helped keep track of my family's finances for varying lengths of time and differing degrees of success.
Mint turned out to be an interesting case. Its homepage promises that "Mint does all the work of organizing and categorizing your spending for you." Which is true, really. Log in, and it automatically fetches the latest transactions to give you up-to-date balances for all of your accounts.
So for over five years, I dutifully logged in every day, checked my balances, and split and corrected any transactions that required it. But the question it took me too long to ask myself was: Does using Mint change the way Casey and I spend our money?