Ladder racks high on the side and stick it forward over the cab.

 

Can you post a visual of this? Not sure what you mean by on the side, unless you mean something like this:

http://goto.walmart.com/c/404739/56...ww.walmart.com/ip/Pickup-Truck-Ladder-Rack-with-Removable-Support-Arms/29389585

 

Yep....exactly that. Cheap and removable when you don't want em.
Most truck bed kayaks i see are shorter than 14 or so.

 

10-4 good idea. Will mess around with it and see how best I can strap the kayak down. Wondering if people run ratchet straps to the front bumper, or if they do it all behind the cab.

 

Pool noodle on the roof and a ratchet strap thru the windows

 

Don’t use ratchet straps on your kayak….use the type that grip with no ratchet….

Like these…

 

Why? Worried about putting too much pressure on it with the ratchet and damaging the plastic hull?

 

Your bed extender with a red flag on your kayak is fine. The red flag is required if you are more than 4 foot past your bumper. I do it a lot with my 15' kayak. The only issue you'll have is if you travel before sunrise or after sunset. Then you will need lights near the end of your kayak since your kayak extends more than 4 feet beyond your trucks bumper. I rigged up some cheapo trailer lights on some pvc. Works great. Also ratchet straps are fine as long as you don't tighten them down beyond snug AND keep them on for an extended time in the hot sun.

This is a 15 foot kayak in a F150 short bed.

 

Kayak tie Down Straps Bow and Stern tie Downs Loops Strap Ratchet Rope Canoe Pulley Hanger Anchor Point Tying Kit

I recommend these if you tie to your bumper or through the cab of your truck. I use straps for my kayak but do not over tighten them. If you lay your kayak out of the bed, can you get away with a red flag instead of the lights?

Perhaps, flip the kayak, and strap to your tail gate and cab using noodles and above strap. Use additional straps for extra security. I am not a big fan of trailers for kayaking. I use my kayak to save money and the trailer is just another expense.