I recently set up a Plex server and started ripping all of my DVDs onto it. There were a couple of hiccups, but overall I've been pretty happy with it. You get

I recently set up a Plex server and started ripping all of my DVDs onto it. There were a couple of hiccups, but overall I've been pretty happy with it. You get a nice netflix-like interface for browsers, it still works great when my crappy internet drops to <1mbs (happens a lot in the evenings, presumably because all of my neighbors are watching Netflix and the local ISP vastly oversold the capacity). And if you pay $150 for the lifetime pass, you get the ability to sync content for offline viewing on whatever device you want + a few other niceties. Ripping DVDs & renaming things to Plex-friendly form is still more work than I think it should be, I'd really like to see something equivalent to CD-ripping software that "just knows" what the disk is by fingerprinting or whatever. In general, Plex doesn't provide anything that I couldn't do with existing (and mostly free) tools, but it provides a friendly enough interface that my wife can use it without help, and being able to sync content to my iPad before a trip and have it "just work" is really nice.