If you are serious about music, you are probably storing it in a lossless format. Most popular choices are FLAC, Apple lossless (M4A) and Windows Media Lossless (WMA); there is also Monkey’s Audio which isn’t as popular. All of these choices have advantages and drawbacks. Both WMA and M4A are proprietary and the only tool that can create them is WMP and iTunes respectively. It is possible to get all of them to play on a non-windows machine, but it’s often quite difficult to do so. Even more difficult is getting them to play or stream to standalone hardware devices which is what you’d want to do at home. And support for portable devices is divisive to the max.If you choose FLAC as the best middle ground, you may want to at least be able to play it using operating system’s audio player. Windows Media Player is not a bad player but it does not support FLAC out of the box. Playing it is one thing, it needs to be able to display its tag as well as edit it. Here I will only mention how to get it to work.Download oggcodecs for your OS flavour – 32 or 64 bit. These are DirectShow filters that let WMP recognize FLAC and some other formats. Also download FLAC support, as this is what will actually allow you to play FLAC files. Finally, download the WMP Tag Plus. This one allows WMP to see tags embedded in FLAC files as well as edit them, and is the best of its breed as it integrates closely with the WMP.Now you’ll be able to deal with FLAC files as if they were any other support format (e.g. MP3 or AAC). One thing still does not work though – you won’t be able to stream FLAC to another Windows PC’s WMP or to a media extender. I haven’t had luck finding a solution for this yet.
UPDATE: as Ben mentioned below, if you use 64-bit OS, you need to make sure FLAC filters from Xiph get installed into a proper folder for 64-bit which is <system drive>\Program Files\Xiph.org because it will otherwise overwrite (or be overwritten by) the 32-bit version.