Taxes are a tricky thing. On the one hand, you have got the constant possibility of being audited for anything on your taxes which does not look kosher. On the other hand, you have also got the guilt of having to ask for some kind of a receipt every time you cut a check to a charitable organization. While most charities are quite used to handing out receipts as though they were candy, it can still feel a little on the weird side to ask for something of that nature. And of course, if you do surrender to the guilt and refrain from asking, you might as well kiss a little bit more of your money goodbye when the tax man comes around next year. If all else fails, you can probably avoid being audited, but they can still get you for several years. And that can end up being really painful down the road, because problems like that always seem to hit you when you are the least prepared for them, like right after your house needs a new roof and your kid needs their tuition paid.
Of course, donating is still a good cause, and it would be wrong to completely shirk it just because you might theoretically be hit with a larger tax bill down the road because of your generosity. While the old saying about how no good deed ever goes unpunished does ring true from time to time, ultimately you should get some kind of personal benefit out of giving to others.
Just remember that if you intend to deduct, you need to get a receipt, if only to be on the safe side. If you get audited and “caught” once (because the IRS trusts no one), it will make you into a more likely person to be audited later on, if the person who reviews your tax returns just gets a bad feeling. While hunches are not necessarily right, they can lead you to a lot of trouble if it involves underpaying your taxes and being charged back taxes and fees for that hunch.