Squezebox + iTunes + FLAC

Mr. Brass, iTunes can't play FLAC so you have to convert the file to something iTunes can play. Load that file into iTunes and play it.

Mgattmch, unless you use a player like Amarra or Pure Music that controls the output rate of Core Audio on the fly you need to change the settings in Audio Midi Interface each time you want to play a file with a different rate. iTunes locks onto whatever AM is set to when you launch it so each time you set AM to a different rate you have to quit and restart iTunes. If iTunes outputs a different rate than AM is set to the Core Audio will resample it.

If you start iTunes with AM set to 44.1 and play a 96 file iTunes will downsample to 44.1 it and CA will pass it through.

If you start iTunes with AM set to 44.1, change AM to 96, and play a 96 file iTunes will downsample to 44.1 it since that is what is locked onto and CA will upsample it back to 96, not good.

One way to avoid the hassle is to set MA to 96 and launch iTunes. iTunes will play native 96 as is and upsample 44.1 to 96.

Why are you not simply using SqueezeCenter, which supports FLAC and up to 24/96? Note too, that unless you are using the Transporter, or the new Squeeze Touch, you won't be able to listen to 24/96, since the other SB devices will only support up to 24/48...

ben's comments are correct. the rest of the suggestions are spinning your wheels unless you switch to the touch or transporter. his suggestion to use squeezebox server is a good one too as i find it much more seamless than itunes with the logitech products and flac is the native format.