Our team has used hollow poly cord a couple of times.
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You can do either. In the past we have generally stacked pulleys (either COTS from McMaster/SDP-SI or homemade), but a single roller with multiple grooves can be a more elegant solution. I have seen various plastics (UHMW and ABS mostly) turned into roller/pulleys on a lathe, and that works well for many.
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We have only ever had problems with barbed connections when people got lazy and made poor quality cuts. As long as you make sharp, flush cuts and fully insert the barbs, you will have no issues.
