I mean 20+ years of experience and all perfectly working C/C++ code and libraries have to be thrown out of window ? Cmon Google. Java is a nice toy, but unfit for production, get real.
Someone has never heard of JNI.
As for point #1, replacing your DRM-laden songs. Now that is typical Apple - typical American corporate beast. They didn't even offer the option, trade up to DRM free (with higher sampling bitrate) for 30 cents.
Incorrect, you can upgrade songs in your library to a higher quality DRM free version.
Really, if you have a server on them big tubes and you're not getting 70,000 login failures a day, you need to improve your page rankings.
Really, if you have a server on them "big tubes" and leave ssh open to the world, you need to keep your day job.
Everybody needs a little love sometime; stop hacking and fall in love!