For the Osprey hookset I really give it to em on the hookset. With the wood plugs, especially the slammer when I'm fishing it on top, I'll wind really fast until I feel weight, then I'll give a hookset. For the osprey, I just pop em right away. My thinking on the osprey hookset is that it'll rip the hooks out of the bait and let it slide up away from the fish, rather than having the whole heavy bait in it's mouth which is easier or it to spit out. Plus, with the re-rigged trebles, it'll have another hook swinging around back there which is sure to get caught on something. Plus, just the way they bite the plugs tells me how to set the hook. For me at least, I've found that with the wood plugs, there's generally a lot of line that needs to be moved, or you don't feel the fish right when they bite it, so I prefer to tighten up on em and then swing. A really hard hookset will do the job also. With the osprey, you feel the fish right when it bites the bait, with no middle man, so you can just set like normal.
-Brian