Gap in "gapless" track when "repeat one" in use

I have some short tracks meant to be played on an infinite loop -- babbling brook sound and such. As you can imagine, though these sound fine when played in a truly seamless loop, if there's even a small gap when the track repeats, they sound horrible.
The tracks play just fine in iTunes -- no gaps, seamless, perfect. But when played on my iPod Classic, there's a brief gap when the track repeats. Just a fraction of a second glitch, but it's enough to change the effect from relaxing to horribly jarring. Unusable, in short.
Is this a known iPod bug, or is there something I can do to fix it? (Yes, I have considered taking the short tracks and dup'ing them a few hundred times in a sound editor to create one big truly gapless music file with lots of repetitions, but that seems like a very ugly hack.)

The term "gapless" when referring to the iPod is usually understood to mean no gap between one track _and the next_ , and so expecting the iPod to manage gapless transitions when repeating the same track is probably asking a bit much of it. Perhaps someone else reading this may disagree...
By the way, I believe that the iPod's gapless feature is designed to work as follows: when you select "crossfade playback" (in iTunes, Edit/Preferences/Playback) each song is faded into the next - except for any albums marked as gapless. (I have not actually tried crossfade playback yet, but I have read about it in other posts.)
You could always try the crossfade playback and see what happens, but I think your ugly hack may be the only answer! Actually, one last thought, how long are these short tracks? The Classic iPod models must buffer the output from the hard drive to the headphones (again, I'm sure someone will disagree ) and if the track is very short, the buffer may not have time to find the start of the track before it finishes. Do you get the gap if you let the track play through to a third time?

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