Where are you running Squeezeboxserver? With Squeezebox system, multi zone usually means adding additional squeezeboxes. Assuming your "larger system downstairs" is a good audio 2-channel system, best bet would be to add a Touch down there. You would then have 2 Touch'es, each can connect to your Squeezeboxserver either via wired ethernet (preferred for reliability reasons) or wifi. The Touch supports playback of 24/96 lossless files (FLAC for sure, not sure if Apple lossless is supported "natively" by the Touch, but if you are running your Squeezeboxserver on a reasonable PC (not your NAS), the Squeezeboxserver can support transcoding from Apple lossless to FLAC if needed). You probably want a copy of ALL your music files available to your Squeezeboxserver - this could be on a drive local to the Squeezeboxserver PC, or I suppose could be available through your NAS.
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