I... don't come from Evanston? As for the rest, I'm not really sure what you're getting at.
Difficult? No. Expensive? Somewhat. But it's actually a patchwork of different services you'd need to sort out, an accountant can't handle all of it (though they certainly can help). There are some online services that are more full-service but it's not cheap. Regardless, if we were planning on having a household worker for the long term, I'd probably outsource the bureaucracy; since we expect this to be strictly a short term arrangement (frankly we have neither the funds, space in our home, or comfort with having an employee) I'm not sure it's worth it.
I wasn't blaming safety net failures on bureaucracy, I was blaming people's low level of adherence to the law on government bureaucracy, which seems eminently reasonable. The financial cost of complying with these laws is likely less than 10% of an employee's gross salary; hardly the end of the world. But the time cost in complying with these laws is dozens of hours of time, which is a commodity I have far too little of.
Also... what's so wrong with having a friend with a tax lawyer? You know my educational background and where I live.
All of my nearby friends are professionals of one sort or another, it's not shameful.