If I do a transaction for no business purpose other than to minimize my tax liability, the IRS will dub this a sham transaction and make me pay the taxes anyway. Similarly, I think sham laws aimed at creating a taxable event for some purpose other than raising revenue, are a bad idea.
I think that libertarians ought to be holding teach-ins on the topic of the health care law, liberty, and the Constitution. Two interesting questions are in play:
1. The role of the Constitution on economic matters. Most people, when they think of the Supreme Court striking down laws, think of laws that restrict the right to obtain an abortion, obtain a gun, display pornography, or avoid seeing a Christmas display on government property. The idea that the Constitution could restrict Congress on economic policy just never occurred to most people. The discussion issue at the teach-in should be whether there should be any restrictions on laws governing economic activity and, if so, should those restrictions be stronger or weaker than what the Supreme Court currently permits?
2. The second issue is the relationship between taxes and mandates. If the government has the power to punish you for not buying health insurance, does it make a difference whether the form of punishment is a prison term, a tax obligation, or a fine? Under this general topic, you can raise the question of what differentiates taxes from voluntary contributions.
It will be a great day when all governance is handled by organizations financed by bake sales.