Ipod Classic with Itunes 12.1 - Warning
First off,
Known issues - immediately after 12 dropped, pretty much all functionality involving Ipod classics was broken. Mac OS recieved a patch that fixed this, Windows has not, and there has been no addressing this issue thus far.
My stuff: Ipod class 120gb 8 years old, windows 7 64bit gaming rig, windows 7 64bit laptop. Gaming rig has been updated to 12.1, laptop was kept in version 11.
The problems: Most common - Ipod will disconnect seconds after being plugged in, leaving no chance to do any diagnosing whatsoever.
Less common - Ipod will show up and be interactable in Itunes, click Sync and get stuck in a never ending loop, stuck on song 1 of X forever, I left it doing that overnight - a good 16 hours - just in case, click restore and get an error 1439 (or similar number, basically same error) Ipod cannot be restored
Least common - upon clicking "restore Ipod" the computer will blue screen, complete system crash resulting in a system recovery or total loss of data
The fix(for me anyway) - use itunes 11 - Thankfully I had an old laptop that still had version 11.something installed on it, I was able to transfer my non-itunes store music to it and everything is just peachy
I reiterate - These are known issues, I have found dozens of forum posts on various websites complaining about just how fantastically broken the itunes 12 update has been, and many people have resorted to downgrading back to 11, a not-so-broken version. But here's the kicker - Itunes version 11.0.0.163 has NUMEROUS problems that result in either failed installation or instant crashes whenever you try to launch it, or if you're lucky just crashes whenever you try and access the Itunes store through it. Good luck trying to find someone to help you with installing these old versions if you run into one of these problems.
If you have an Ipod classic and a windows 7 computer DO NOT update to Itunes 12, it will not work, and most support operators will run you through hours of diagnostics just to prove that your ipods hard drive isn't crapping out from age.
iPod classic (120 GB), Windows 7