I've found that once your tags are in order and files named properly, they tend to "just work" with pretty much everything. Ibasso, iTunes, Cowon, A&K, Android devices, XBMC and Sonos. For automated ripping, artwork, file conversions etc. I use dBPowerAmp. Horrible name, HUGELY powerful software: http://www.dbpoweramp.com/ - Honestly, Head-Fi should sort out some sort of member discount as any and all audiophiles should own this software.