That being said, it seems "freer" to me to tell the IRS what my financial situation is rather than let it dictate to me what I owe, and then have to fight the government in order to take a deduction for donating to GoodWill or the Salvation Army. I'm splitting hairs trying to play devil's advocate here.
That's very similar to what's described in other countries. The government provides you with prefilled forms. In the basic scenario you sign and return. In a more complex scenario you amend it, sign it and return.
As a bonus, they could make it software and offer a way to file/check online--but I'd be happy if they at least did it via the mail with paper.
It's your money, you can do what you want with it, so sure, give it away to charity if you want — but WTF does that have to do with taxes? You pay taxes on your income, and then you can give away some of what's left; it's not the IRS that wants you to give it away, so why should their cut be affected by that?
I'm pretty sure the US is alone in this weirdness too, as in so many others.
That being said, it seems "freer" to me to tell the IRS what my financial situation is rather than let it dictate to me what I owe, and then have to fight the government in order to take a deduction for donating to GoodWill or the Salvation Army. I'm splitting hairs trying to play devil's advocate here.