Time consuming is a good way to put it as it's quite involved. Not all shops want to do this during the season - some don't want to do it at all - keep checking around. But again, a lot of this depends on your skill set and comfort level. It's probably not worth getting into the nitty gritty on a forum since you can look at that by downloading the installation directions of the particular model you are thinking about. You'll want to check the amount of "fall" you have based on where the chain/rope is going to drop and decide if you want/need a horizontal or vertical windlass. Research some of that and study some installation directions to see if it's something you want to tackle. This is not going to be one of those things were you watch a 5-minute Youtube video and then go do it - there's a lot more to it.
Does your current anchor roller support leaving the anchor "stored" in the roller without causing any damage?