For media server, I recommend Serviio, and not _too_ worry about video encoding that much (on-the-fly transcoding, but a few mkv files do have issues, depending on how they were encoded). And Linux/Windows/Mac version are available for free.

Maybe he can try to find a job in a MMO game industry, whether it's a developer, content developer, tester, etc. So he could still play and work :)