The key here is that something is up with the rips. If the original CD had gaps (which I assume it did) then those should be present as 2 second (usually) silences at the end of each track. Thus, when you play the album back you get gaps as intended. If there aren't any gaps then either (a) there were none on the CD to begin with or (b) the ripping process removed them. In case (a) there's nothing which can easily be done as the point of the squeezebox and lossless encoding is to reproduce exactly what's on the CD as closely as possible. In case (b) reripping may help, once you figure out why the gaps are missing.
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