Analog and Digital

Hi, I'm new to the whole Raspberry Pi thing (but not to decent audio projects) and aiming to build a Raspberry based Squeezebox client (player). I know Squeezebox pretty well, but nothing about Raspberry Pi.
Can you connect both a DAC and a Digi board to run simultaneously from one Raspberry Pi? I'd like to have the option to use either digital or analog output without making any changes "on the go"
Also, what is considered to be the best software to use for talking LMS?


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