First off... 8" huddleston on 30 lb braid... ARE YOU INSANE!!! Then again... I don't trust braid of any size :)

Hook sets... Obviously the fish has to get the bait in it's mouth before you stick them. It sounds like your fish aren't eating it very well. With big rubber baits especially, the fish really needs to fully inhale it to get a solid hook set. Once they do have it in their mouth set hard. It takes some power to move the bait towards the front of the fish's mouth and the hooks to sink in. A greasy scent helps here.

For the most part it sounds like you just need more aggressive fish than anything. When they suck the bait down their throat things work out more smoothly.