There are different schools of thought on hook setting technique. Some say to not set the hook right away and wind down until you feel pressure and then use a sweeping hook set especially when fishing with fluorocarbon for football jigs in situations where you're casting out far and deep but even also for flippin/pitchin. Others say that you should set the hook right away as soon as you feel a bite i.e. soon after you feel a bite, lower the rod as you reel up the slack as quick as possible and set the hook immediately. I've experimented with both, and regardless of the scenario, setting the hook as soon as you have a bite has resulted in higher percentage of hook ups in my experience. I believe that as quick as a bass can hit a lure, he can also spit it out just as quickly. Sure, there's cases where a bass could hit a jig and hold onto to it for a while, giving you the leeway to take your time, but I'd rather not take my chances. Senkos are another story. Senkos are so soft and full of salt that a bass will hold onto that thing and swallow it every single time if you wait too long, but I think a bass can detect that a jig is unnatural and spit it out.
You should also check the weed guard. Depending on the manufacturer, some weed guards are really stiff and some are really limber. You can clip off some strands to make it less stiff or you can fan out the guard or do a combination of both. You should always trim the length of the weed guard so that it does extend passed the barb of the hook.
There are times where I don't shorten the trailer to get the largest possible profile, but to make the lure more compact, you can cut off some of the trailer. I've seen a bass strike just hit the tail of the trailer before. With a more compact profile, there's less of a chance that he'll miss the hook.
Your set up should work fine, but I feel that a Dobyn's heavy is like other manufacturers MH. Flipping jigs have thick wire hooks and often times, stiff guards. Perhaps, a Dobyn's XH, 50lb braid, and bone jarring hook set might help, too.