Thanks guys. I feel more educated already after reading the feedback and watching the video.
Our anchor is the "break away" type. Got two zap straps on the eye nearest the rear of the anchor. As I understand it if the anchor gets hung up the zap straps snap and the anchor will release it's angle/bite. Makes sense.
Also makes sense to drive forward close to over the anchor before pulling it up. Yesterday I was heaving on the anchor without much luck and actually pulled our BOAT over the anchor myself, then the anchor released once the angle was right. A lot easier on the back to drive the boat forward, then pull
I really like the design of the Anchor Caddie. Basically what I want. Was looking at pre-fab one in Cascade and they only carry the type (for hand bombing) where the anchor drops into a recess. This seems fine for transport but I've heard they are a pain to deploy as you need to lift it up and out to get it to drop. I like how with the anchor caddie type you can release it from back near the wheel. I don't plan to order an anchor caddie as with the exchange rate I think I could do better local.
Gonna check out Balmer Fabrication (Abby) and Primus Metalworks (Chilliwack) tomorrow. Both advertise that they make/install bow rollers. Will also check out AJ Ventures as I've heard good things about them. I'll pick who I have the most confidence will make the roller the way I want and if the price seems fair I'll go there.