While I was in NYC over the summer I got to attend a plethora of shows. Matt and I do prioritize spending our money on shows so we definitely spent a good chunk of our budget going to the theater, but I do have some tricks on how to see a ton of shows for the smallest amount of money possible.
First off, my FAVORITE website that I constantly use when figuring out what to see next is BroadwayForBrokePeople.com - It is a non-flashy website that has every show running listed in a nice grid format and all pertinent information alongside it. They have theater information, opening/closing date, performance schedule and my person favorite column "cheapest tickets". I love that all the information is on one page in one easy to read format.
As for the different methods I use to see shows:
TKTS line - The original discount booth (started in 1968!) for Broadway shows, here you can get same day tickets for a wide variety of shows, musicals, and plays both off Broadway and on Broadway. There are 3 locations for TKTS tickets, one in time square, one downtown, and one in Brooklyn. You best chance at getting good tickets here for great deals is to come early and wait in line before the booth opens everyday, rain or shine. They also have an app you can download on your phone that will show you what tickets they have in stock that day.
Today Tix - my favorite way to get tickets. Instead of waiting outside in the heat or cold in the TKTS line you can go online and buy tickets through this app up to a week in advance for amazing deals. Then once you buy them you don't have to worry about printing them, 30 mins before every performance one of their staff waits outside each theater to hand deliver your tickets to you. The shows they have available change everyday so you definitely have to look at it regularly, but we got some awesome deals on here. You can also enter certain lotteries through the app. We did so everyday and never won, so don't count on it.
Lotteries - We scored a ton of our tickets through the lottery system. Each theater has its own rules if they do the lottery but most tickets won through here are around $30ish each and the seats awarded are scattered around the theater. Sometimes you luck out with 3rd row seats center, sometimes you end up in the balcony with a partial views. Its total luck.
And a bonus shot of Matt killing it outside of Kinky Boots.