[sliverstorm]

IMO there exists behavior I'll call "bad faith tax reduction". You might not be doing anything illegal by the letter of the law, but maybe those education expenses you deducted, went to a business you own (or something like that).

An exploitable tax code is like an exploitable software package. Yes, the software gave you everyone's personal information in the database. But maybe it only did that when you ran a buffer overflow attack to escalate your permissions.

Setting aside exact numbers, I figure a decent razor for whether you're being honest is whether you mind other people learning about what your tax return looks like. I deducted my property tax and my mortgage interest; I will tell you that freely. But if I had twelve offshore shell companies scooting money around through various tax loopholes, even though it's not illegal I probably wouldn't want anyone but the IRS to know...