The concern I have with giving them money is: They're going to get shut down, sooner if not later. Big media have had people raided for less than what they're doing, and laws are written (again, by big media) to put them into a legally gray area.
Morally I don't think what they're doing is wrong. But the US government is in bed with media goliaths, and the two work together to shut down re-hosted content (even in areas where re-hosting MIGHT be fair usage).
Playon doesn't rehost the content. It runs on your computer and automates the process of capturing the video stream from a website. So, you have to _actually wait for the entire video to play_ to have it fully downloaded because its nothing more than a screencapture in essence.
The whole thing is a little flaky, but I'm really pleased with what it cost me ($60 if I remember).
Morally I don't think what they're doing is wrong. But the US government is in bed with media goliaths, and the two work together to shut down re-hosted content (even in areas where re-hosting MIGHT be fair usage).