Good rant.
Each of us draws our own lines we won't cross. For example, I won't set up a foreign asset protection trust.
If you are uncomfortable engaging in sophisticated planning, then don't. But blowing them off without understanding is ignorant. I'm showing you techniques which are valid and useful in certain contexts. For example, there is no reason whatsoever that asset sale stockholder agreements are not part of your practice.
Playing the audit game happens in the real world every day. It's getting worse because the IRS is underfunded. I'd like to see far better enforcement because I'm tired of seeing fraud and pathetically incorrect tax positions which ultimately succeed.
I consider your snarky criticism of my attitude to be hypocritical. For example, I presume you don't tell your S clients to take all the income as salary because they obviously earned all of it via personal services. The idea of a lower salary is there. It works in practice. What are you gonna do when the issue is before you? Like I said, it's a matter of degree and each of us draws our lines in different places.
I tell my clients I can't beat fraud. I assume they want to achieve similar results without committing fraud. So I do all my planning assuming the IRS is fully aware of the facts -- which in my view means I am not playing the audit lottery. On the other hand, it is a factor in the client's decision-making process.
I consider taxation as theft, a necessary evil. I have no moral considerations in tax planning unless a third party is involved. So I pay extra attention to ethics as my only limitation.
Many transactions can happen in alternative ways which generate different results. That's tax planning. If the transaction meets all the black letter law, then the only issues are judicial doctrines designed to protect the spirit of the law. As a lawyer, that's the gray area in which I dwell.
I've often heard it said that filing a tax return is like filing a pleading. If you want to see ludicrous stories, read some pleadings. Almost all are filed in (supposedly) good faith.
Again, inform the client and let the client decide. You're not the IRS. Please don't act like it.
Steve