multimodal commuter
Join Date: Nov 2006
Location: NJ, NYC, LI
Posts: 19,808
Bikes: 1940s Fothergill, 1959 Allegro Special, 1963? Claud Butler Olympic Sprint, Lambert 'Clubman', 1974 Fuji "the Ace", 1976 Holdsworth 650b conversion rando bike, 1983 Trek 720 tourer, 1984 Counterpoint Opus II, 1993 Basso Gap, 2010 Downtube 8h, and...
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I think you'll find a thread in the tandem forum in which they address the use of disk brakes and other hub brakes as a drag brake. Basically, the problem is that drum brakes and roller brakes and even disk brakes don't dissipate heat well enough to be reliable as drag brakes. Should be find for emergency stopping, though.
Have you looked into carrying the kayak on a Xtracycle with a longloader? It would almost certainly handle better than a trailer, though I'm not sure you could carry quite as much gear.
At any rate there is a huge thread on DIY trailers and hitches in the utility cycling forum.