I haven’t really thought about or felt this recently, but I definitely got a similar feeling a lot when I was first getting into punk and indie music. I remember seeing Gang of Four at Coachella in… 2003 or 2004? and that was one of the first times I realized that their music on Entertainment! probably sounded completely different when they performed it live in the 70s. The Coachella show left something to be desired, but there was clearly a much different vibe and more thorough depth to their sound (and in writing this, I’ve just remembered that they even thought their records didn’t reflect their live sound, enough that they released an album of re-recordings of their old songs).
You can hear similar thing by comparing Joy Division’s studio work with their live recordings. Or if you’ve ever seen Mission of Burma, comparing that to the old recordings…
In the past year, I’ve also struggled with this a bit in my own music… I had some song concepts that I wanted to do proper production on, but play live in a completely different way, and it’s turning out to be harder to reconcile the two than I’d originally thought.
With all of the high-precision control that you can get with modern DAWs, it’s really easy to over-produce a track, or fall into the trap of trying to make things perfect, rather than treating the system as a means of capturing a live performance. I find that when I fall into that hole, it’s even harder to figure out when to stop, or to call something finished. Especially if I accidentally let myself think about about how meticulously edited and comped most mainstream music is these days.
I think there’s probably also some motivation in the opposite direction to “just be done with it already”, and to move forward on new things, rather than spending production time revisiting the old.