I won School of Rock on the second try midweek a little while ago, but I think it's a bit risky when you only have 2 chances, since it's online. They do have a rush too, though, so you could just line up in the morning... From what I saw when I rushed Color Purple across the street from the Les Mis that rush is also pretty easy mid week if you get there in the morning... Something Rotten also has a rush, but I've never tried it.
I haven't done the Matilda lottery since its online, and Fun Home not since I saw it when it opened last year (it took long to win then but it's been a long time since).
Overall, since your only here for 2 days I think it's safer if you use the rushes instead of the lottery, it's just saver if you get there early (School of Rock is a hard rush, for the other 9 or even 9:30 should be fine, they might even have rush tickets later in the day)