I hear what you're saying, and understand it, but that's not the way I was taught to handle donations at PWC (one of the big 4 CPA firms). It's not that difficult to work backwards and put the pieces of the puzzle back together and realize you didn't have room in your budget for 8k in cereal. Technically speaking, up to a $250 donation, you need a cancelled check or receipt from the organization...250+, you need a little more documentation. And technically speaking per the Pension Protection Act of 2006, you do need record of donating to a religious organization...but to my knowledge, that is rather lax enforcement. So with the understanding I have, and the 13k tax discrepancy on my father's taxes that turned in to 109k after penalties and interest 2 years later, which he has now been paying 1700 a month on for the last 3 years, I tend to err on the side of caution when it comes to the IRS. IMO, the IRS is no one to screw with, but if you're comfortable with telling them you lost your receipt(s) and think that'll save you, by all means don't let me talk you out of it. Here again though, this is all moot if you don't get audited, so you're probably safe if you don't raise any red flags and stay within the tolerances. But as I said, $2400 in donations without receipts seems to be about where I noticed the IRS starts sniffing. But you're good with only receipts if it's 20% or less of you AGI.
Disclaimer...last time I was 'in the know' on this stuff was 3 years ago, so things may have changed.
