Hey Jtcf-- Glad we share the same surreal effect of our listening rituals! I enjoy those sessions immensely.
Mapman-- I agree wholeheartedly. I got completely lost in the sound of my red plastic all-in-one record player in my early teens. Now, in mid-life, I'm a lot more discerning and it takes more at this level to "get lost". I still love my gear, but only because it does what it does in reproducing musical events that can sweep me into another place and time.
Rockadanny -- Oh you nailed it. Those few (by percentage) recordings that are engineered so well that all the engineering disappears along with my room are so precious that I buy multiple copies (now that's just crazy, right?). Last night I was listening to Bill Evans' Waltz For Debbie on an original pressing and it never fails to move me, on my system. I've heard it on lesser systems that weren't put together very well to little effect, if any -- just didn't have the magic. After all these years of stumbling around this expensive hobby, I'm so grateful to now know how to put together a really musical rig (for friends who ask) at many price points.
In my experience, I have noticed that I have several listening modes:
Casual  where I'm cooking in the kitchen but it sounds like Bill Evans is in my living room. I love that. Bill plays his heart out for hours and I don't even need to feed him dinner.
Critical  Where I notice minute aspects of the recording, venue, and gear and I'm either impressed or not, but definitely keeping score in my head.
Teleportive: The Holy Grail of this hobby (for me). I put on a magic LP, close my eyes and seconds after needle drop, I'm gone. Teleported to a venue, front row center, where a favorite musician is holding court, in total disbelief that anything can sound so beautiful or anyone can be that talented. This happens about once a week in the Man-Cave.
If we're not having fun, something's not right.