I find that my interest in listening is sporatic. Sometimes its obsession, other times I couldn't care less about it.
When to listen... I have a routine where every Friday evening (after work and before dinner, I sit down and do the bills. I have my 2-ch listening room setup so there is a 'listening' couch positioned opposite the speaker wall, then behind that is my desk - where bills are paid, payments recorded, stuff is ordered, etc. System sounds just as good from the desk as it does from the couch. Time-wise, its good for at least an hour or two - even during periods of disinterest.
However, I must admit... for me it really is more about the gear. I know most will gasp at me saying this (but true for me) - I'm not listening to recreate a feeling of live events, and some would say my choices of music are questionable. I like well-recorded bassy enjoyable tracks that bring-out the details of the system. Who's playing and what's the name of the song aren't something I would usually know. Matter of fact, I'm much more likely to recognize the album art than the artist - blasphamy, I know. 😎
Setup your listening space so something that frequently needs doing is getting accomplished when you're listening.