LOL -- 'raises flags.' ... You can't live your life in fear of the IRS. Assuming you're law-abiding, so what if they audit you?
Have you ever actually been audited? The world doesn't end. They ask for info, you give it to them. It's like worrying about traffic on the 405. Get over it.
Just the hassle of an audit is a pain and the cost could be a few thousand. They can go back 7 years. Do you have all your receipts for your expenses and travel going back, did your client reimburse you for those expenses? Were you compensated per diem. Was that business or personal, remember that far back? You're guilty until proven innocent. No fun ...
The mere chance of it should make you feel like being short the SPY puts on a bad day. Keeping lawman out of your business is also big part of your risk management and shouldn't be ignored.
Again, have you ever actually been audited? I have a feeling you're speaking from ignorance, though I could be wrong. Re keeping lawman out of your business -- they'll get into your business at a time of their choosing. You can't prevent it. Always be prepared. Don't rely on "avoiding red flags."
Family members and my cpa are ex-auditors. Carry on raising red flags and let us know how your audit went. BTW you know a red flag when you seen one.
No, they just hear stories about the big bad gubment and the "friend of a friend of a friend" who got totally screwed by the IRS. Sure there are a few a-hole IRS agents, just like any other field, and certainly you can dig up a few stories about nightmare audits. But it's losing the forest for the trees to unnecessarily pay tens of thousands of extra dollars in taxes every year because you're afraid of setting up a legal entity that might subject you to audit. Of course if they're not consistently making significant profits, they can go ahead and conspiracy away if it makes them feel better about themselves.
Not so simple. They ask for info, you give. They ask again, you give again. They ask for more, you give more. Then when they owe you, they don't pay. (I'm still waiting 8 months) Better to stay under any radar, particularly when it comes to trading issues. The IRS is under-manned and under-funded. You don't want to get involved if you can at all avoid it.
Fill out this form with your fill name and see what happens. https://www.irs.gov/pub/irs-pdf/f3949a.pdf