I've gone in phases -- I spent close to a grand on iTunes (well, probably less, I purchased about 1,000 songs, but some of them were on $9.99 albums with more than 10 tracks) in the first couple of years I had an iPod. Then I discovered eMusic and downloaded some great stuff, but I just ended that, mostly because of Spotify but also because they kept changing their TOS and a few small labels I liked pulled their stuff. I also went through a music blog kick, stuffing an external hard drive -- a move I'll probably regret, as I can't figure out how to format the drive and make it work with Time Machine, so I'm sure to lose it all sooner or later. I'm not sure if I'll start paying for Spotify once my six months is up, but I probably will.
I got a record player in 2008, re-bought the (mostly hardcore, surf, and psych) collection I carelessly sold off in 1998 or so, and now buy a good amount of vinyl. I try to keep it under control, and Spotify helps with that -- I listen to records for free a bunch of times and if I really love them I'll purchase the vinyl. I kept all of my pre-2005 CDs but the only CDs I've bought in the past five years or so have been kids' music, mostly to play in the car. I feel a ton of inexplicable affection for cassettes, but I have no desire to own a tape player. Some guy in my neighborhood was selling a desktop 8-track player with a complete collection (Led Zep, Wishbone Ash, Boston, etc.) and I briefly considered buying it for work as an affection.
As far as books go, I am a physical book guy. I have a Kindle that I occasionally use for scripts, and that I loaded up with a couple hundred public domain books. Sometimes I'll take it on a trip if I'm almost finished with my book and can't decide what to read next, but that's about it. I've been reading Pride and Prejudice for nearly a year this way.