I need to install a trolley on my new yak. I've watched YouTube videos on it and all. My question is, how hard would it really be to do it myself?

I did it myself using a steel ring, two pulleys and two caribiners. Didn't even drill anything, I used the front and back handles to attach the pulleys to, and then paracord for the rope.

Yak gear makes a complete rivet on trolley kit. Easy as pie to install and works great.

It's not difficult at all man. Just get one of the kits with quality pulleys. I put mine on about a week after I got my first kayak. The hardest part was convincing myself to put the first hole in my yak.

You can also do the "no drill" method.
Pretty sure a few guys on here have gone this route.

no drill method

I did the no drill method and it worked great for about 2 seasons, until this past weekend when one of the plastic pulleys simply snapped apart on the chord in high winds(I did have 2 drift socks out, but still). I'm replacing with a metal set of pulleys for this weekend, but it's about the easiest install of anything on a kayak so I wouldn't hesitate to do it yourself.

do this 1st. drill your holes later if you still want to. i havent drilled any holes for my trollys either. broke an old worn our carabiner 1 time in some choppy water. i paddled to land swapped it out and was back in action.

No holes for my trolly system either. I followed the instructions from Palmetto's kayak fishing blog (the link posted by ETBA above) Works just fine.

The BassRustler

I was worried about drilling holes in my kayak at first and it wasn't an expensive kayak either... So I said to myself, lifes short just do it. Nothing last forever anyways, most of the time people are just worried about having to re-sell it later to upgrade and don't want anything to cause the kayak to loose value (modified). Just like cars no one really wants a car someone has been modifying because it can loose its reliability.

The yak gear kit is really nice. My buddy did his himself and it works perfect and looks proffessionaly installed. He said it was easy to install. I made my own but I'm cheap...

If you are unsure about it, swing by APT this weekend and I can walk you through it. Its no big deal as long as you take your time.

SpiderJig a lot depends on what kayak you have and the access you have to the inside.
If you have the tools and the correct trolley parts and pieces it's normally a easy project.

Ive got a WS Ride 135, as far as tools are concerned I have your basic garage tools. I think Ill try to do the no drill route

If you've got a Wildy, this no drill method from Hook 1 might serve you perfectly. I adapted it to my Jackson Cuda 12, and it's worked great as a no drill alternative.

https://www.youtube.com/watch?v=xDuhYbG-T4Q&list=FLHQDGmXylj1UBTcBw5H88Lg