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If the Westside plan tells you when to use the sled, of course do it then. As far as distances, just start walking with it, it would be useful to tell you do walk 100ft with it if you are dying after 60! So see where you are at with your own level of fitness. In general, say "I'm going to walk to that driveway and back" or whatever you want to gauge your progress with. Then, measure how far you went so you have an objective to beat.
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