Don't beat yourself up over it. They don't just jack up the prices when the supply is low, they jack them up whenever they think they can squeeze a few (or more than a few) extra bucks out of us.
Last year, Garbage did one of a very few headline shows for them here. That's a no-brainer for me. Tix went on sale, and the front balcony seats where I like to sit at this venue (and the floor was standing only, so that wasn't an option) were $69. Oh wait, that's $69 face value. If you wanted the front balcony seats except for the outer parts of the last row, those started at $153. And stayed that way until the day of the show. No thanks. We ended up getting seats in the back part of the balcony for like $50. It's to the point where I try to avoid going to shows at TicketMaster and especially LiveNation venues. There's no enjoyment in the buying process anymore. Especially when I compare it to what is one of my favorite venues, who handle their own ticket sales. No dynamic pricing. No ridiculous fees. Actual paper tickets sent in the mail, although you have to pay an outrageous (checks notes) $1 for that.
So after reading the thread at TGP where they were getting shredded for their "Dynamic Pricing" model, I figured something out, and started to watch. As soon as these tickets went on sale, I logged in to check prices, I mean, like 1 hour after it opened. They had whole sections of the floor showing as sold out already. I checked front of the balcony (very good seats in this venue) and "middle" of the floor (rows 15-25 or so). There was almost nothing available. I assumed he really had almost sold out immediately.
Then I went back to the TGP thread and read some more about what they were actually doing. After the initial opening, I logged back in a couple weeks later. Whole rows were available on the floor and the front sections the balcony, and were listed as some BS like "just came open, won't last" etc. And prices were higher than at opening. Apparently that didn't go as planned because a few weeks later even more rows were available, and now back at the initial price. I watched those for a few days and little by little they all disappeared, so that at least appears to be legit "sale" of tickets. Then two weeks before, I've talked to a few friends, have one who wants to go but not sure he can, I get on and price 2 seats again. Now there are even more "new" seats available that never were any of the 5-6 times I looked!
2 days later, he confirms that he can't make it. I go back in to buy one, figuring I'll go by myself. They had some back of the balcony and extreme side tickets available. The side was are bad seats, I'd never take them. They were $35 higher than the week before. The back of the balcony seats had gone up $50, to MORE than the rows 15-25 seats I looked at earlier.
What people at TGP said confirmed what it "looked like" to me. They release partial tickets up front and make them look like their selling out fast, so people will jump. Then they release more later. And then right before the show, if there are only a few left, they jack the price up and release more. However, if there are plenty left, they will, or might, lower the price. I verified this as well, but watching tickets for one show that never did sell out. The worst tickets dropped $25 by the week before the show, because there were a bunch available (only about half sold).
So, instead of saying "here are all the tickets, and here are the prices for each based on where they are," they release some, then some more, them some more, to strategically make it look like it's selling out quickly, and then later act like they just came up with more and it's "last chance" pricing... but sometimes it backfires and if someone isn't selling a lot you might actually get a ticket cheaper.
It's time to stand up against this. Get the artists on board by saying we won't come to shows if ticketmaster controls the tickets, etc.
Oh, one more thing. There is a long standing proof (I have had it for years) that for many years before this Dynamic bs, Ticketmaster was in bed with all the scalpers. I remember one time when I was 3rd in line (camped out all night. Remember those days?) at the ONLY venue selling tickets to a major show, and couldn't get anything in the front section (which seats over 1000). Later that day, all the big scalpers had front section tickets available online for premium prices. One of my friends is one of them. He told me he and all his other scalper buddies all got the best seats to every show in town, because they paid the boss at Ticketmaster.