For me, it usually went something like this:
1. First I bought the 45 of the single because I wanted to hear the song.
2. Then I bought the LP because I wanted to hear the whole album.
3. Then I bought the 8-Track because I wanted to listen to it in the car.
4. Then I made a cassette from the LP or bought the cassette because the cassette was better than the 8-Track and more portable than the LP.
6. Then I made more cassettes and gave them to my friends.
7. Then I bought the CD.
8. Then I lost the CD.
9. Then I downloaded a 128 MP3 from Napster because I wanted it on my computer.
10. Then my hard drive failed and I lost the 128 MP3 from Napster.
11. Then I bought a new turntable, got the LP out of storage, and listened to the LP again.
12. Then I bought the CD again and ripped it to a FLAC file and put that on my computer.
13. Then I downloaded a 24 bit version because it sounded better than the FLAC file ripped from the CD.
There are many variations on the theme, but it usually went something like that. Mostly, I'm just not satisfied until I've paid for the the same record about four times in my life.