I been down this road, for the last 3 years. You'll find some large grass fields you can hunt with a large group. Here's one issue I see, everyone else that wants to hunt with a battalion of buddies will hit the same areas. So you can have a good shoot if it's opening day, or if the crops came out within a couple days of you hunting. Otherwise you have educated birds that already been through the whole song and dance. Inevitably there's a commotion trying to get the regiment ready. Doors slamming, yacking(seems almost inevitable with 16 guys), etc. Most of the birds have already ran west to Custer County, or at the least are on high alert.
Another point to reiterate, from what I've seen hunting in larger groups equals less shooting per hunter. When a bird finally gets up you're watching someone 5 people down the line blasting away. Or if the bird gets up right in the middle, then it's like the anti-aircraft guns in Berlin lighting' up when a B-52 formation flew overhead. That rooster has good odds of getting swiss-cheesed.
Another observation, it can be confusing to the dogs. Don't get me wrong, they're still gonna hunt up birds. But often they'll run down the line as they see another orange hat to check in, sometimes they all end up on one side, etc. Then you've got guys, and it only takes one, who walks too fast and is somewhere in the middle. A bird gets up then, you can't shoot, no safe line of fire. I've also seen the dogs working scent, and the line moves too fast so you're almost passing the dog as he tries to unravel a scent trail.
Here's my advice, if you're dead set on hunting all together, find a spot to do it first thing in the morning, but definitely have a plan in place to split the group.
Bring a little grill and plan a field lunch, plus back at your lodging at night you'll have plenty of time to tell old war stories and cut up on each other.