i did experiment writing little AMOS programs to automatically make samples loop. take a reasonably long sample, fade it out in a portion at the end with a sine-squared profile, take the same length portion at the beginning and fade it in the same way, then cut the beginning off and mix it in over the end. Results vary, but at worst it sounds like "wowowow" rather than "dingdingding" which is certainly an improvement...
i also experimented with chords made up in whole-number ratios, so you can get perfect-looping samples created from short waveforms in about 1k each, although i never tried actually using it in music, it was just a quick and dirty test. One of these days i'll get round to trying it...
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