Yes, lifting the "far" end of the boat simply can't be done without outside help or until the "near end" reaches the end of its range of travel, because more pulleys are turning when that end moves. The system takes the easy way out. Good thinking!!
It's still not really a problem - just a bit of an inconvenience - as already explained, but your perspective now makes it clear that simply trying to reduce pulley friction won't make it work any better than it does now.
Kayak Motor Kit
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