Windows Media Player
does support FLAC through free Directshow plugins (and has done so for years).
Making support available in Windows so that's not seen as bloat by the 99.999% of users who have not even heard of FLAC would also rest on the format being *completely unencumbered* by patent and license restrictions. Let's not forget how even MP3 and Adobe's free-for-everybody-except-Microsoft PDF played out.
Portable devices that support lossless, or indeed >300kps playback of any type - including VBR MP3, would greatly aid introduction to market.
The French Qobuz.com store has been offering choice of lossless and lossy formats for some time, and there are no geo-restrictions for download. You can also redownload anything you've bought from them should you lose your copy.