I'm usually awake either later at night (go to bed at 1 or 2) or early in the morning (wake up at 2 or 3) and those are my listening times; when I'm not transferring LPs (which of course requires me to be in front of the computer) my go-to setup is my iPod Classic hooked up to a CMoy headphone amplifier feeding my Sennheiser HD600s, and I listen in bed or, rarely, on the couch, in the dark. (The iPod is one of my best purchases in the last five-plus years, easily.) My general limit is two albums per session, doing nothing else and listening closely -- I've developed a long attention span; before I had this setup I was distracted easily.
I typically listen to a new or unfamiliar album several times until it just feels like it's time to move on. Usually one of the two listens is to one of these discs I'm repeat-listening to and the other is something I already know, not repeated.
I can't listen to music in the daytime. I get no pleasure out of it and I can't engage with it (when I'm inclined to listen in the first place).
NP: Bob Dylan - Blood on the Tracks: how is "Jack of Hearts" any worse than "idiot weeee-yind"?.