My first time I came to NYC for vacation in November 2012, I was there for ten days and had a limited budget and only saw four shows. The way I saw two of them was via SRO lines. I missed out on rush tickets for Once because I was too far back, but I scored a $27 SRO ticket as those were given out to those next in line. It remains one of my favorite Broadway shows. I pretty much cried through the whole show. It was with the original cast after it cleaned up at the Tony's.
That same trip I stood in line for Book of Mormon. I got there 6 hours before they they started offering the tix in 40-degree weather. I was first in line. Young woman got there soon after and we waited the whole time. So we both got $27 SRO tickets (we entered the lottery too, but no luck there). The show is great (another one of my favorites), but my favorite part is she and I are still Facebook friends. That was a true bonding environment. Anyone who is willing to do that would probably meet the compatibility test for friendship with me. Lol
On the other end of the spectrum, 2 years ago I wanted to see Hamilton. So while in NYC, I made friends with someone (hmmmm...I sense a theme) at the Hamilton lottery. Tried twice. Never won, of course. We ended up going to Times Square Marriott Marquis ticket concierge booth and paid $375 each for (originally $65) seats in highest level of Balcony. Zero leg room, long legs, bad knees, almost constant knee pain. Despite that, Hamilton, remains my favorite Broadway show experience.
i just spent $250 on DEH (w/ Ben) and $413 for Hello Dolly! In November. Hoping they'll be two more to add to the above list.
I have no shows I regret spending money on although some obviously were bound to be better than others.