I'm writing this not knowing where your pup is in his training/development, so I'll apologize if he's further along.
8 months is pretty young for some dogs, so be careful spending too much money on a membership and a ton of birds just yet. I've see dogs ready to hunt at 8 months and dogs not ready to hunt until their second year. Transitioning from sight to scent pointing can be a challenge for some dogs as well. I'd look for a place that sold chukar as well as pheasant. An ornery rooster can scare a young dog. Chukar are big enough that a young dog has an easy time finding the, they don't typically run, are good flyers, and won't spur your dog. The DNR offers a dog training LC. Another option is look into getting one of those LC's and finding a place that will sell you birds and planting birds, you can plant birds in the designated DNR dog training areas. Something to keep in the back of your mind, early season in WI is rough on dogs. Scenting conditions are terrible until the first solid frost.
How I've always done introduction to shooting. Take your pup out for a good solid romp, get him really tired, and then take him to a skeet range. Start way back, 100 yards or so, every time there is a shot praise a few treats never hurt either, if the shots alert the dog but he isn't alarmed move 10 yards closer every few minutes. If the dog is uncomfortable/showing signs of nervousness ignore him (don't reassure him in anyway) and move back to where he is calm again. The objective is to get the dock withing 10 yards of the range w/o paying any attention to the shots. This may take one trip or it may take 20 trips.
Where is he at in whoa training? Are you using an E-collar? Teaching hand signals is a must if you're going to hunt spooky grouse. If you wan't to get together I'll be happy to help. I will say one of the weak points for my dogs is backing maybe we can help each other on that training point
I'm a real big fan of letting a puppy be a puppy. Spend as much time in the field with him as humanly possible, you will be shocked how much your dog will figure out on its own.