The song limit could be a problem for you.

The other issue I believe is only an option—you can have your files replaced by ones from iTunes (which is really a form of illegal song laundering for people who, unlike JPB, have stolen all their music and have subpar files), but you do not have to.

To be honest, your best bet may be just to unsync albums that you NEVER listen to, so that you have them on your hard drive, but not on your iPod. That does not sound all that unreasonable, given that there is still a fucking shitload of music on that goddamn iPod. Don’t be so greedy, JaPaBo!