Hello Jake,
Yes - only the Advanced Edition supports multiple audio outputs, and you can only use the Advanced Edition evaluation for evaluation purposes, and only for a reasonable evaluation purposes. Hence if you want to use to use multi-channel audio output on an ongoing basis you would need to buy a licence for the Advanced Edition.
You can only have one Hauptwerk installation on any given Windows installation at a time (although the 'Hauptwerk (stand-alone)' and 'Hauptwerk (for MIDI sequencing)' desktop shortcuts/configurations do allow you to have two sets of independent settings).