How to see as many shows as cheaply as possible?

I currently reside in LA but am moving to DC. As it's a short(ish) commute to NYC and I have a free place to stay there, I'm considering seeing as many shows as possible. However, I'll be on a pretty tight budget and, while I know certain shows have rush tickets, I want to ensure that I'll be able to see certain shows. How do you find the cheapest way to see as many shows as possible? Also, are there any shows that really require orchestra seats in order to truly appreciate them? I'm really excited to be able to access Broadway and Off-Broadway shows and I want to take advantage of my proximity to them.

Playbill.com has a page that explains everyone's rush and lotto status

Off-broadway - http://www.playbill.com/celebritybuzz/article/144419-Off-Broadway-Rush-Standing-Room-and-Inexpensive-Ticket-Policies

Broadway -- http://www.playbill.com/celebritybuzz/article/82428-Broadway-Rush-Lottery-and-Standing-Room-Only-Policies

Dicount site: broadwaybox.com

Must see from the orchestra? That's really about preference.

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There's ways to see most shows for under $40 however you can't be picky about where the seats are or if there are even seats at all. I would sign up for HipTix through Roundabout as soon as you can so you can start getting those $21.50 seats. They are located in the rear mezz though. MTC does $30 under 30 also which would be good if you are under 30 years old.