kevin you should be fine with the file size all my mp3's play just fine. Really though if you want to save space it doesn't need to be any bigger that 128kbps. You really can't tell the difference if it's any higher, with the speaker or headphone that comes with your pearl. For programs if just use dbpowerAMP Music Converter. There are plenty of free programs out there. I just don't know of any off hand.