To ensure self leveling with a winch there needs to be no more than 18° of angle at the bow roller to the total width of winch drum. In this case as the winch drum is 300mm, the distance to bow roller needs to be 948mm or greater. With no intermediate roller.

There are several things wrong with this set up.

The first is the rode is pulling almost 90° around the roller. This reduces the winches pulling power a bit.

The second is the distance between the bow roller and winch is too short to allow self leveling. Obviously this is dictated some what by boat design.

The third thing wrong it the intermediate roller shorts the distance even further from the bow roller. It is also far too narrow, to allow any hope of self leveling.

The fix in this case is to swap "anchor up" rotation of the drum, so the rode goes over the top of drum, not under it. Remove the intermediate roller, and raise the bow roller slightly to allow a direct line from bow roller to winch. That will allow a direct pull on the rode, with a distance of about 980mm.

It will also stop the rode grinding away at the anchor well edge. The fact that the bow roller isn't even square to bowsprit, does my head in.

I going to make a new bow roller, repair the old holes and start a fresh.

See the rode is bunched badly in the middle. 

Firstly, it started with the rode laid evenly right to the edges - but soon went to what you see here, bunched badly in the middle. 

I think Several factors are causing this.

1. The intermediate roller is not wide enough, or is too far back; so does not allow a straight line from the bow roller to the side of the drum. Getting a wider roller would help, although I havent seen any wider roller.

2. The distance from the bow roller to the drum, is too short; however it is dictated by anchor bin to bow sprit.

I have 100m of rope/chain; which allows anchoring up to 50m depth - thats enough for me. I could increase rope from 100m to about 150m, before the chain exceeds the space in the drum. Generally, getting a drum big enough is important - I have seen many drums smaller. Mine is a Viper Pro Rapid 1000w, which has a relatively big drum.

SO, I think the moral of the story, should be - know exactly what it will do, and make sure its installed as you want. NOte - I didnt take much notice of how it was going to be done; in my case, the boat maker, used a roller thats too narrow - but luckily its been ok for me.