What are you actually referring to? In my experience, it takes a pretty serious mistake to get charged a fine (it’s never happened to me despite mistakes). The IRS just charges (fairly reasonable) interest if a mistake results in underpayment. And IIRC, they pay interest to you when you overpay too.
Much of my experience may have been shaped by my experiences with Chicago. I vividly remember how painful it was to have to call them up every month in order to pay them. It was 2016, and I forget exactly what the reason was. But autopay was somehow sufficiently painful to set up that the path of least resistance was to set a reminder in my phone of "Pay taxes to city" and deal with sitting on hold.
If it sounds unbelievable, I don't blame you at all. I wouldn't have believed it myself until seeing just how Kafkaesque "dealing with the government" can be. Especially when penalties are involved.
For the rest of my family, it's a little awkward to find out. It's mostly on my wife's side; my father was always very fastidious about taxes, as most families of most HN readers probably are. I only wanted to point out that there's a large number of people where this isn't true.
I'll try to dig up direct answers for you. Thankfully most of this pain has been not-mine for many years now.
I think most of the fear of the IRS comes from rumors like your post.
I think in reality, a way to get the “civilized country” (as referred to by another poster) tax experience is just file an incomplete return, the IRS will bill you the correct amount along with a negligible “fee” (interest) a few weeks or months later.
Maybe doing this repeatedly would upset the IRS, I don’t know. But it definitely works a few times without issue.
Out of curiosity, what monthly tax did you pay to Chicago? The city does not levy income or property tax. Most people will only ever pay Chicago sales tax or things like a yearly “city sticker” car license fee.
