Originally Posted by NYBanker

I reiterate: You should take every mid-gray-area deduction that you can relate to business with a straight face. Period. If the service has a problem, they'll let you know. <emphasis added>

Absent those failing to disclose large amounts of income or taking a large amount of deductions that fail the straight face test, there's nothing wrong with agressive tax positions. No one should pay a penny more than they absolutely have to.

(The following comment is directed at more than the question on lounge dues.) Being conservative on your taxes, for the sake of "avoiding an audit," is not a prudent strategy, assuming you are a rationale economic actor.