Pay close attention to your quench/squish. My understanding this is a major factor toward reducing spark knock. Whether that applies to detonation with your boosted plan or not I can't say but it probably does.

Note that a hotter block (coolant routed to head first) means a hotter piston. Much of the heat transfer out of the piston is through the rings and skirt into the cylinder walls. Also, I would be a little concerned about the coolant flow paths in both the head and block with reversed flow. For example, is there an intentional flow path with increased velocity up from the block near the spark plug to keep it cool in the factory configuration? I have no special knowledge, just some formal education on these subjects. I applaud your efforts. Comments are meant to be encouraging!