e57,
Um -- I obviously wasn't telling you anything you didn't already know. I apologize for stating the obvious.
As for the Sidekick, I don't think it will tell you anything useful unless the symptom is present (in which case your ears and a butt set will tell you the same thing for $1K less).
The bummer is that it's perfectly simple for the telco to isolate the IW during loop testing, because there's a function in the NTU to do exactly that. Hal is probably right that it's just unofficial policy to deny the problem until the customer gets squeaky enough.
In the case of the letter I wrote, it probably helped to compare (unfavorably) the quality of service to that of a third-world country. Or maybe it's that I addressed it to PacBell's CEO.