Ours (2015 Windsport) is a little tricky, and think it's probably overdue for a lube job. Extends just fine. If fully (but not over) extended, it needs a little "help" to get past that first movement - just like my creaky elbow. Have my co-pilot push retract button (or I use the remote, if I remember I have it) while pulling down slightly on the lowest joint. Once it starts moving, it's off to the races. Just my experience, and one more item on my maintenance list. Your mileage may vary.
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