Katherine, thank you for the reply, and thank you for taking the time to actually read the fact sheet. I learned the hard way about the "session" approach recognized by Wisconsin. Therefore, I keep logs when I gamble and I am in a position to prove the losses I might incur. Let me give you an example: I sit down to play video poker. At one point I have a lucky hand and win $2,000, which generates a W-2G. However, by the end of my session, I am only ahead by $500, despite that one win. I would expect that the TurboTax program would recognize this situation. For instance, once I indicate I have a W-2G, the Wisconsin program would ask if I was keeping a log of my sessions? If not, it would default to the $2,000 gain. However, if I answered yes, it would initiate a routine that would have me report the sessions and only include the winning ones in my income.
By the way, I respect the fact that you are an accountant living here. I am not an accountant; prior to retiring, I was a tax collector. Because of that background, I'm not shy about digging into the details of this stuff. (Also, I too have always found DOR staff very helpful. This is a TurboTax problem, not a DOR problem.)
Thanks again.
