Good network setup of music collection in iTunes

My setup consists of a windows server with iTunes, a windows htpc, a 32 gb 4S and a ipad3. Same apple id on all. Originally I connected the iPhone to iTunes on the server and later also the iPad by USB cable, so these are paired or not? Now only on wifi.
My music collection was mostly in flac, so I converted them to apple lossless and put the in the iTunes on the server. Getting the htpc, I just took a copy of the iTunes on the server and placed it locally on the htpc, but it means that covers are not replicated. Also the phone is filled with some music, but thou I have checked the box for down convert, it will not do that.
So now I wonder what a good setup of the music collection will be, so changes are propagated from the server lib to the htpc and iPhone and iPad, while buying though iTunes will also go to all devices.
Any recommendations?

After further investigation, it appears this problem is related to rebuffering. iTunes 7 appears to lose sync when it rebuffers music from the hosting machine (Mac Mini). There is NO fix or workaround that I've been able to come up with.
As to why iTunes needs to rebuffer at all and why it can't maintain a constant, uninterrupted flow of music to the remote machine over a GigE network, I'm not sure. The streaming buffer size is set to LARGE.
Both machines are vitually running idle when playing music, so not sure what's impacting buffering. Seems like the streaming bug and iTunes 7 has only made it worse.

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