I am wondering if the effort vs. reward ratio is actually worth syncing an iPod classic to Musicbee. I just got a laptop that runs Windows 8.1, I've been using iTunes with various Macbook Pros since 2007. I found iTunes to be annoying and glitchy on OSX and I don't even want to know how glitchy it is on a Windows machine. I love Musicbee so far and I love how easy it is to convert files to basically any format you wish within the GUI.
Here are a few questions that I would really appreciate answered from those who got the iPod classic working with Musicbee.
1) Do you have to Jailbreak the iPod in order to sync with Musicbee?
2) If so, what software would you recommend using to do so?
3) Do you find that your iPod works well with Musicbee or is it more trouble than it's worth?