Linux and music

Hi everyone, Happy new year! If anyone has any advice for me on the following, it would be very much appreciated. Problem statement: I'm reliant on Windows for music. I own an iPod shuffle, and am reliant on iTunes to download music to this device. What I would like to do is buy another, non-Apple music player, and fulfill the following requirements; 1. Run a music program within Linux (Ubuntu / Unity) 2. Download music legally within Linux 3. Load my music player from within the music program 4. Convert the music from iTunes/Apple format and have it available to the Linux music program. What are my options? Regards, Kathy