What bugs me is that quite a lot of things are not available. I ripped my entire CD collection and uploaded into Google Music (not sure if that feature still exists). I have all this music available but I can not find it on other peoples google music. So if I share a song, they get an error. Most of this music is nothing special and quite mainstream but if I search on other peoples devices I can not find the songs on…
This is why it's so important that we resist pressure to upload everything to the cloud. Buy a 64 or 128GiB flash drive and put your whole collection there. (plus one probably for backup). Copy it to all your local machine(s). Copy the important stuff to your mobile.
Collections are not static. I discover new music every once in a while. Syncing with cloud makes sense; it is just that you could be the owner of the hardware behind the cloud, to maintain privacy or you encrypt the data in the cloud (or both, and use one cloud as backup).
You could use rsync or something with a flash drive though. Android smartphones will happily eat microSD cards containing hundreds of GB of music.
Which means the iPod Classic 160 GB is finally obsolete. However I think you can hack those devices anyway, to put in a new 2.5" SATA SSD (if they eat SATA).