ABout 300 lbs. of trailer in the slipstream behind the car vs. a kayak on the roof obstructing the airstrem sounds like a toss-up, burden-wise. The roof mount is far less complicated to execute, but loading and unloading are a pain.
RV supply stores will sell a universal wiring converter with a "flat-4" connector for cars with amber turn signals, like the Prius. Last time I checked, Toyota dealers sell them (for Camrys and Highlanders, mind you.)
Trailers don't have seperate turn signals, they simply flash the brake light on the apprpriate side like American cars have done for years. It is a pretty easy DIY installation accomplished by splicing behind the tailights, usually accessed via plastic doors in the cargo compartment for bulb change access. Without a Prius wiring diagram, you'll need a probe to find the proper wires for left turn, right turn and taillights. But Toyota wiring uses standard colors across models, so if you buy the kit from a Toyota dealer, the color codes will probably still apply. But still use a probe to be sure.
I found this hitch from Draw Tite, so several somebodies are doing what you propose:
http://www.drawtite-hitches.com/hitchsea...
They are a reputable company, so I'm sure they made sure the attachment points were strong enough. The shipping tie-downs used for lashing the cars down when they are shipped from Japan are generally what these hitches attach to. Four bolts and a big torque wrench and you're on your way. Not sure if you have to notch the bumper.
But trailer hitches are hard to hide. The first time you pull into a Toyota dealer for service, don't be surprised to hear that your Prius' warranty is null and void.
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