My BroadwayDirect track record is pretty shoddy, but I've hard worse if not similar luck with TodayTix lottos.
Lost every day for Hamilton since Feb day 1; recently stopped due to being too busy to remember to check personal email at 4pm every day.
Took me forever to win American In Paris and unfortunately not before Robbie left. Won On Your Feet! in Jan (first or second try?) but was in a meeting and couldn't pay in time. Lost a couple of times after that -- lost interest. Never tried for Aladdin/Wicked/Lion King -- no interest in seeing again. Haven't tried Cats yet.
In general, winning for me seems to come in streaks as well, cross-platform (like I might win a combo of Jujamcyn, Telecharge, and TodayTix in the same month, then total dry spell for months). I typically either win within 3 tries, or it takes several weeks/months of entering every day to win (or locked out completely, show closes).
So I'm surprised when people complain they've "entered 5 times already and lost." I gotta roll my eyes so hard. It's why it's called a lottery...