Me: How much do I owe?
Gov’t: You have to figure that out.
Me: I just pay what I want?
Gov’t: Oh, no we know exactly how much you owe. But you have to guess that number too.
Me: What if I get it wrong?
Gov’t: You go to prison"
https://twitter.com/jordan_stratton/status/11181414550616719...
PDF: https://www.ussc.gov/sites/default/files/pdf/research-and-pu...
Then I just sign a form and return it instead of slogging through the bullshit that Intuit et al has lobbied for.
Apart from that, IRS workers are just like workers at any other job where throughput is a primary metric: They just want to close cases quickly with a resolution. That may mean penalties and interest rate if you screwed up or were actually trying to avoid what you owe. They're not taking you to court and prosecuting for $100k if you're working with them to fix things though. In the end, they don't much care if the settlement takes 10 years to pay off $200/month at a time as long as they can close the case as resolved.
Source: 1) I have a friend who was an IRS lawyer and then a tax attorney. 2) I know someone who went bankrupt and came to long term multi-year agreement to pay $50/month.
The "solution" they deem as legal is to create a whole new bussiness dedicated to do X, or refuse to do it. And to my eyes X and Y are related (like doing a security audit to a web and building a web), but IRS don't think so.
It sounds complicated, but paying about $100 for the TurboTax edition that handles small businesses will make it fairly easy. Yep, they've got strong regulatory capture in this space, but business income isn't always straight forward so I would consider ~$100 well worth it. Though I'm sure that some dead-simple home businesses really wouldn't need it.