Last night, a colleague and I took some students to hear the Civic Orchestra, a youth orchestra sponsored by the Chicago Symphony. It marked the end of a semester where I had attended the CSO at least every two weeks. I had been going increasingly often in recent years, but this summer I made a Facebook friend who plays with the orchestra and generously offered to track down comp tickets for me, meaning I could go much more often than I could normally afford.
The experience of being a “regular” has been different in ways that I didn’t anticipate. It’s not merely quantitative — being “in it” to that degree has deepened my appreciation and (I think) understanding of classical music. Without having to shell out for every ticket, I have been more open to whatever they happen to be playing, which has broadened my horizon beyond a certain early 20th-century modernist rut that I have been stuck in for a while. I’m becoming a better listener, to the point where I don’t feel like I always need to familiarize myself with recordings of a piece in advance.
The biggest change, though, is that I feel more confident in what a good performance or interpretation is. For instance, I heard Muti conduct Pictures at an Exhibition and felt that they kind of “phoned in” the finale, which other more experienced fellow attendees confirmed. Similarly, I heard Neeme Järvi conduct a program of Prokofiev and Sibelius and felt it was one of the best concerts I’d ever heard — and for the first time ever, I overheard multiple people on the way out gushing about how great the concert was. I was even so bold as to skip directly to a standing ovation after Denis Kozhukhin’s virtuoso performance of Prokofiev’s 2nd Piano Concerto.
The shift in my perspective is similar to one I experienced a few years ago for visual art. I was teaching Shimer’s fine arts course and hence paying more concentrated attention to art than I ever had before. I always enjoyed it and was vaguely knowledgable about the basic outlines of art history, but it is proverbial that you only really know something through teaching. This happened to correspond to a period when I was doing a lot of travelling and so I got to visit several of the greatest art museums in the world within a short span of time. That level of immersion turned out to be a qualitative shift.
The root of my renewed interest in classical music — making it my primary musical diet instead of one thing among many — also corresponded with my teaching of the course, but my real immersion experience only came in the last few months. To make sure it sticks, though, I anticipate continuing with the same regimen for the foreseeable future.
An und für sich 
Amazing when you see symphonic music for discovery and not to hear favorites, or even the familiar. I’ve been lucky in a way similar to you, in that through marriage, I’m distantly related to Sasha Kazovsky, a founding member of the Ariel Quartet, https://www.arielquartet.com, and whenever they are in NYC, my wife and I get tickets. Most of the time, I’m completely unfamiliar with the pieces, but they almost always amaze, and I’d never have seen them had I not been given these chances. Since she’s family, she stays at our apartment from time to time, and to hear the way a musician speaks of music was also a revelation: they are fiercely involved with it. Not like a fan–the way I understand– but as someone who is intimate with the very notes, and how she loves to talk to other people who feel so strongly, and differently, about the same piece. (I heard tell about the auditions when one of the original members got married and moved to Japan. How hard it was to hear all excellent viola players and having to choose between them. The behind the strings view: fascinating.) Enjoy. It’s expanisive.