I have not heard the Weiss Medea DAC you're using so can't comment directly on it though it does have a good reputation.
However, I run my Squeezebox through a Lavry DA-10 DAC and am very pleased with my system. I settled on this combo 2 1/2 years ago after going through quite a bit of equipment (including a Transporter) for several years preceding that. I've had no urge to change anything at the source end since.
Also, double-check your settings in the Squeezecenter. There are a bunch of possible configurations and some (such as streaming and decoding formats and volume normalization, for example) can adversely affect the sound quality.
However, I run my Squeezebox through a Lavry DA-10 DAC and am very pleased with my system. I settled on this combo 2 1/2 years ago after going through quite a bit of equipment (including a Transporter) for several years preceding that. I've had no urge to change anything at the source end since.
Also, double-check your settings in the Squeezecenter. There are a bunch of possible configurations and some (such as streaming and decoding formats and volume normalization, for example) can adversely affect the sound quality.