NO WAY I absolutely HATE iTunes, particularly its user interface. MediaMonkey is better but still not quite right. I only use iTunes when I have to, grrr, stupid Apple and yet more of their crappy proprietary technology.
Have you considered getting a DNLA compliant device? And installing a DNLA server? You can again get network devices e.g. Buffalo do a DNLA server on one of their NAS devices. Just a thought, might be cheaper to do something like that.
xbmc: XBox Media Centre, some software that would run on an old xbox or other computer hardware to play movies and music etc. I used to talk about this a lot...