I share Bob’s experience.
Toslink is the worst of all, highest jitter on every single device I tried.
And while Squeezebox is indeed isolated from PC in every way simply due to the fact it is the Ethernet that is used to transfer blocks of data that are assembled into digital signal, the execution of Squeezebox, from power supply to clock, is very poor, and this clearly results in very high jitter on any digital output, SPDIF on Squeezebox is poor while Toslink is horrible.
There is no such thing as jitter immune DAC.
It is silly to even consider using Squeezebox as digital source into any but the cheapest DACs.