I would start with Foobar... its free. Others will tell you to use other programs more tailored for Apple products and you may want to end up that way, but initially get Foobar 2000 and get an external hard drive, use Foobar as a server program and see how you like using files.... a decent DAC can be had Cheap that will beat any consumer level cd player and completely agree that your week link is loading lower quality files such as MP3.... Flac should be the lowest quality that you should look at and if you, I prefer WAV and if you decide to go with a Program more Tailored for Apple, you will most likely end up using AIFF files. Read, read and read a bit more, the info is out there, when it comes to DACs and how they connect to your Ipad, research only the newest info, even info from just 2 years ago can be obsolete. I hope this helps, Tim