As a longtime small business owner, who is fairly proficient at preparing my own taxes, I am uncomfortable with the legal means to document gambling wins/losses. There are certainly grey areas open to interpretation throughout the tax codes but I feel almost anything I have claimed for my business could be validated if enough effort was put in during an audit. A gambling diary/logbook?? Even with lots of details these entries could not ever be fully validated. Sure there may be some record that you have visited a given property, you could pull receipts from the cage or take pics, but at the end of the day you would more or less be at the mercy of the auditor.

I really don't want to be audited so I think I'd rather eat the tax liability at this point. Now if it gets to the point of tens of thousands in W2Gs I'll have to figure out a way to get more comfortable. Maybe those of you who have been through an audit can speak to your experiences with an auditor regarding gaming activity documentation?