In the interim, I’ve been able to manage things reasonably effectively by centralizing everything into one massive library on my media server, and using Salling Clicker as my whole house remote control streaming to Airport Express stations. Works very very nicely.

However, this still doesn’t adress my problems in wanting to take a subset of the library out on my PowerBook. What I’m really dreaming of is a way to have my powerbook treated as an iPod, and automatically sync up a selected set of playlists in both directions. That would be the ideal solution, but is probably not being currently supported due to push back from the majors since this would effectively give you a simple means of copying or cloning an iTunes library to an easily exploitable hard disk. Yes, we know that it’s easy enough to hack the contents of an iPod, but it’s not natively visible out of the box.

I guess that the approach is that you should be using an iPod as the remote device in all use cases, rather than another computer.

I’ve gotten around some of my issues by using OS X Server to host the media account’s home directory so that it either syncs to the media machine in the living room, or I can log on interactively, although that does make for some synchronisation issues when you’re logged on twice at the same time.