This is the same problem Im having, and with little experience in this im not having any fun
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I can see the content through the pc's but not the 360's
the path I have is volume_1/video/tv series/dr who/season 1/ (as an example) since I have only put dr who on there as a test maybe it's the length of the path as described above.
Other thing is that it wont recognise the title of "beyonce" or some of the artists which in the subfolders there are no characters etc, but it just displays them as "other"
I tried the twonky then discovered you need the "telnet" and other stuff but stopped at the part where the telnet did not work after reading a post warning you can brick the unit......

By the way im using 2 x maxtor 250gb in a Jbod configuration, like I say totally new to all this so if anyone can give me a pointer or another way to start, I dont mind starting fresh, formatting etc I'd be very grateful.