I actually tried to do this before. I put her on shuffle and I wanted to see how many days of music I had.
I was going bonkers thinking:
OMG I HAVE to listen to (insert song) but I couldn't cause Ayu was on. (I tried not to skip some songs but I couldn't help myself XD) I did that. I could do it again though, but listening to Her beginning stuff and the stuff she has now isn't going to make me like her new stuff any more. It might make me not even like it anymore because I'm comparing them too much.
@Jon: you're right I do think that is really sad, and I do think you are missing out. I have half the mind to force you to listen HIKKI, L style. (those who have watched Death Note ep. 15 and up know what I mean)