I've read about people who tried that and ran afoul of the IRS for not having paid estimated taxes along the way that made up at least 90% of the eventual tax liability. I'm not trying to skirt any rules or fudge anything here, but don't want to pay more than required (who does). I've run my own business for decades and am well versed in paying estimated taxes. I just need a reasonable basis for this new activity.
To that end I need to have a well-documented process and record-keeping showing I'm following it. From everything I've seen, that's a key element to stay on the IRS good side. Then I need a professional opinion on what will qualify based on case law to be a reasonable approach to estimating the taxes quarterly, and what a "reasonable" salary would be. So many of the cases I've found out there on this topic start off stating "THIS CASE CAN NOT BE CONSIDERED PRECIDENT" in screaming text. It's almost like every case is a one-off decision.
Not a comfortable place to be.
