I finally decided to get into the whole cloud music thing. I'm not an apple person so itunes and icloud were out, even though all my music sits on an old 80GB Ipod Color. Yea, one of those OLD ones. It still works though, and I was surprised to find that after sitting unused in my bag that it still fired up as the battery had not depleted yet.
For free, Google seems the way to go. I looked at Amazon and may still give them a go but for right now I'm testing on Google's platform.
I figured I'd post up my trials and tribulations for others if they are looking to do the same, so I'll update this as things pop up.
1. Import worked fairly well, I didn't have the speed problems that a lot of others complain about. I couldn't in any way import my songs purchased from Apple though, and they didn't do the matching that that Amazon used to do or still does. In fact, I don't think Google matched a single song I have with their library so my entire library is counting toward my usage statistics.
2. Playlists have a stupid feature. You can actually add the same song to the same playlist multiple times. I'm not talking about the same song from different albums, but the exact same song. I thought the shuffle wasn't working but low and behold, I did actually put the same song in twice. Silly stuff Google.