As with all boat projects, preparing and installing the bow roller was a real pain, but I'’m very happy with the results.
 

141stuff This project will mount my 25lb. CQR on deck, and provide an easier way to raise and lower the anchor. I began with a Kingston plow anchor roller from binnacle.com. It is similar to the Windline rollers, but less expensive, free shipping, and no tax. It’s a relatively short roller, as I didn’t want to clutter the deck.  The Triton’s toe rail requires either cutting into it, or building up a platform for the roller. I opted for the second, and found a block of African Mahogany I would cut, sand, and varnish

I tried different configurations and overhanging distances from the toe-rail edge (which is quite challenging on its own). I decided to mount the roller so that the  forward attachment would screw directly through the wider flat area of the toe-rail at the bow, while the rear would be screwed through the wood base and deck. The slight cantilever would protect the bow from dents caused by the anchor bouncing around, being raised and lowered, etc.

141tryout
141holdstar
141holdroller

Next was the tricky part. I wanted the wood base to closely match the toe-rail curvature so it would fit snugly against it. It took some cutting, sanding, more sanding and cutting, until it was close enough where minor imperfections would be masked by the caulk. I then drilled the holes where the screws would sandwich the wood between the roller and the deck, and applied several coats of  Interlux Schooner.

141curve
141varnishing

I drilled the holes in the deck and checked to make sure my hardware would work and be easy to tighten from down below. I used 3/8” machine screws, round head to minimize chafe, accompanied by large washers to serve as backing (WC boat, no core to worry about), lock nut washers, and nylon threaded nuts. I coated the bottom surfaces of the roller and wood block with Lifecaulk, and squeezed them tight via the hardware. Cleaning up the caulk was a mess, but the bedding compound served to transition the flat piece of wood and roller with the angled toe-rail and deck.

141base

Voila!

141starno
141basefar
141starfar 
141starboard
141port
141head on