I would go with a simple anchor trolley. Either buy a kit, or make one. Wet hands is not a big deal, you are in a kayak, you are going to get a little wet.
Once you have used your kayak a bunch, and have developed specific needs and preferences, you can pour money into specifc rigging options. for now, I advise keeping it simple. http://palmettokayakfishing.blogspot.com/2012/02/diy-no-drill-kayak-anchor-trolley.html
I did something similar to this. spend $15 and drilled no holes. It works great.