I am currently trying to sell my parents on the idea of cutting the cable cord, as they are retired now and cannot afford their $150+ monthly bundled services anymore. They've just migrated away from their land line (finally), and now have even less of a reason to keep all those useless services.
The trouble is, the online streaming market is still very fractured. By that I mean, different providers offer different shows. Some even offer different episodes of the same show, when compared to other providers (to illustrate this, here's a hypothetical: A show like NCIS may offer the 5 most recent episodes via CBS.com, Hulu may offer all past seasons but only to Hulu Plus subscribers, Amazon VOD may sell you them instead, etc).
My parents, being old and impatient, have little to no tolerance for menu-heavy systems that require lots of footwork to find the content they want.
Rather than having to surf around to iTunes, Amazon VOD, Hulu, Netflix and finally the individual TV network websites, if in the background, PlayOn could cull the available program lists from all providers and combine them into a master program list by title #-Z, so folks could simply find NCIS, and then be presented with a list of seasons (in the case of TV), and then a clear and easy to understand way to find each episode something like "Episode 1: Pilot (4 sources)" and when you land on that, it gives you the text description (synopsis, box art if any, etc) and a list of providers such as, "1. Amazon VOD ($2.99), 2. iTunes ($29.99 Season Pass), 3. Hulu Plus ($X/mo. sub), 4. Netflix ($8/mo. sub), 5. CBS.com (Free)"
I realize this could require a significant amount of development work to create, but finding some way to mitigate the fractured nature of the market would go a long way to providing some much-needed convenience.