> deciding I didn’t want to see a show in a venue biger than 500 seats or spend more than $50 for it
I've reached a similar conclusion. I've broken my rule a few times, but just about all of them just reinforced my belief in my rule.
Here I tend to aim for venues where the tickets are $25-35. I'll order a couple and invite someone. I've had some of my best concert experiences this way, surpassing the large concerts I've been to by orders of magnitude.
I also find that in most cases, the sound is much better at smaller venues. That is, there are good spots and bad spots, but you can easily move around to a good spot and then it's really good. The large 2000+ venues I've been to have never had good sound, just decent at best.