Would particles for every song help? This thread talks about a tool the author created for making particles automatically for concerts, etc:
https://yabb.jriver.com/interact/index.php?topic=100436.0I don't currently use Theater View (because I use a Mac), but I have a (very) small collection of music concerts. My solution was to make MKVs like you did. But then I used MKVToolNix to automatically break the big MKV file into individual MKV files at the chapter breaks.
So instead of having one file for each concert, I have 15, 20, 25 files; one for each song. Tagging these wasn't too hard, but it did involve *some* manual effort like cutting and pasting the song names from an external web page into the meta data of each song in MC.
So my concert view shows me all of the songs, along with thumbnails, at the top level of each concert. It's very easy to go directly to the song I want to hear. Or I can just select to play all, and it will play each song sequentially.
I'm not saying this is "the answer" for you. I'm just sharing my experience. Good luck.
Brian.