There's a piece of software called "Plex" that basically lets you operate your own private streaming service. You load it up with music and video files, and then you can connect to it from your phone or TV or laptop and play them back.
As I understand it, it is common to set one of these up, fill it with your own legitimately purchased media without doing any illegal circumvention of effective copy-protection measures, and then not only use it yourself but also hand out logins to your housemates, immediate family, extended family, friends and lovers, and so on.
Assuming that these streams to your buddies are all private, rather than public, performances, and that you only actually make one "copy" of your media (which you put onto your server much like you would put a legitimate copy from a CD onto your iPod), does one need any sort of special license to do this? Or is it legal to do with media you just buy at the store?