This works well for me since most of my collection is in FLAC format on the server. Obviously transcoding MP3 to ogg will have losses. However, assuming you have a FLAC collection, you just need to set up a flac to ogg transcoder. I used a single stage of:
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oggenc --quiet --quality=9 -o - %s
This also required oggenc to be installed and symlinked from the subsonic/transcode directory (at least on Linux, I can't say about Windows).
I've tested by CD rips of Led Zeppelin I and Pink Floyd The Wall so far, and they are playing gapless.