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Just an idea:
If you get Plex (a media center solution) and point Plex at your Library folder then this will let you stream all of your media from your laptop / iOS device when you're on your local network as well as when you're out and about. (It negotiates the quality depending on the connection).
It automatically scans the folder for new files and presents them in a nice library view for you.
It's really meant for people that have loads of movies / TV series / music that they want to serve to multiple devices / watch at friends houses / on the bus etc. would work for this too though.
Anyone here from elgato? elgato... gato... gato... to ..... to