So, my friend and I both entered today, and actually had another friend enter as well to increase our chances... and we ended up ALL winning, so this must be pretty easy to win. Judging by the amount people picking up lottery tickets (there was a separate line) they seems to have a lot of them.
We were in Row H, side mezz, which is assume is the $55 seats (didn't check), but considering it so easy to win and there aren't any discounts I think it's still a decent deal. The view was actually really good! The mezz has a large overhang and it steep, so I felt pretty close and had a good stage view. It helped that the 4 rows in front of us were empty.
I'm not really sure on what basis they're assigning the lottery seats. It seems silly to fill up the theater from the back, considering they are only giving out the tickets 30 min before the show so they *could* be flexible with what's available or not last minute. We ended up moving down a few rows at intermission. So I think it's definitely weird, but I liked the seat and overall happy to pay $40 for that seat and the show, which I didn't love but thoroughly enjoyed!