Onhwy61 - I share your approach a lot of the time, though I'm not quite as organized about it. I have several Sony CD Changers controlled through a software front-end that allows for all the categorization you describe. Sometimes I use the software front-end, sometimes I just turn one of the changers on, hit Random and then play. It's like having my own radio station and I find that the "surprise" of what comes on next greatly adds to my enjoyment. I'm not sure why but if I consciously decide to listen to a song from the past it feels like being in a rut, whereas if it just "comes on" it feels great. It also mixes old and new which is great on many levels. It's probably not the last word in technical quality, but it sounds pretty darn good and it really puts me in the frame of mind that the music is everything.
I always have the choice, which I regularly exercise, of picking out a CD to play straight-through. I agree that there is something about the context of the "album" that is valuable and adds to the experience. After many organization schemes, I finally just put everything in alphabetic order. I usually choose based on style and instrument - I love music where the electric guitar is front and center but it's not always what I'm looking for. Sometimes I want vocals, sometimes I really don't.
I also share the technique of keeping the most recent purchases in a pile by the system to play more regularly until I'm familiar with them. Finally, I have a 12 CD changer in my car that I regularly change the contents of. My music collection (~1000 CDs) gets a lot of use. -Kirk