>>>My only experience with this was a $1,500 tournament (non-poker) win which I got me a 1099 for $1,500 which I could not offset

One of the things I always found amusing was the fact that a slot player can get a 1099 for a $1200 win (even if he has $2000 in the machine) and a table player can cash in thousands of dollars in chips and nobody bats an eye