Welcome to the forum! Moving to Mobile Electronics section. I'd take a look at DoubleTwist. It has multiple versions, and multiple levels, and is highly configurable. I just use the free version, but there are some that have a price. I don't have a Gen 5, but I use it with my phone. It is highly compatible with just about everything, and is the best I've ever used. i keep 2,500 albums on my phone's microSD card, and it connects to whatever I plug it into - any vehicle, computer, etc. Smooth and flawless once configured, and will automatically convert m4p files to mp3 on the go. It also has many other abilities, and it's the best such app I've ever encountered. Go look at their site and see if it will work for you. Whatever you decide, be sure to let us know.