Winamp sucks because it’s been co-opted by AOL Time Weiner. If you’d still rather run Winamp try AIMP as it’s an open-source alternative (from the copyright-agnostic commies in Russia XD) built from the original Nullsoft code base that formed the early versions of Winamp.

Most any media player app (except Windows Mediocre) can add files to your iPod IF it’s set in “Disk Mode,” that is, as a pseudo-USB device that you can even put other files on without affecting the player functionality. iPod Touch and iPhone, unfortunately, don’t offer this option, at least not as of last I checked; it only works with regular iPods like the Classic and Nano.

Not sure if there exists a dedicated media player (like the iPod) that plays FOSS formats like .flac and .ogg. Would appreciate it if someone could put up a link. :)

Windows. iTunes a close 2nd.

Both are “#2.” XD