I haven't used the Stripmeister but there are a few things you might try.
You might have the cutting wheel set down too far. Too much downward pressure can cause the wire to squeeze of to one side or the other.
You might try cutting the cable into two foot long pieces and see if they feed through the machine better.
See if the plate on the front with the holes in it is adjustable. Tinker with the adjustment. Try setting it a little high or a little lower than it should be and see if that makes any difference.
( I get some wire that feeds better when the front plate is set a little lower than it ought to be. )
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