Between my husband and myself, we've won a few lotteries. Whenever we are in NYC, I will go through and pick out holes in the schedule where we could fit a show that we don't already have tickets for, and then we both enter all of the lotteries that we're interested in for those times.
Our most recent win was Groundhog Day - he lost, but I won, and we ended up sitting in decent seats in the mezzanine. I thought it was nice that you were able to choose your own seat, but I imagine that's only because the sales were not great. We both got loser emails for the following day (for that lottery, you can enter for a few days at a time in advance).
We also won for Matilda and Fun Home, after a couple of tries a piece. For Matilda, we were on the extreme side of the orchestra in the second row, and for Fun Home we were on the side of the theater, close to the "back" of the stage, about four rows up from the floor.
Of course, that's three wins from literally dozens of entries, and those wins are all for shows where it was clearly fairly easy to win the lottery.