Like Turk, I would recommend WI tho I am not exactly sure of the present timing re the rolling sine curve of ruffed grouse population ups and downs in the upper great lakes region.
Recommended solely due to your home location and the simple desire you have to be there and learn.
I would differ a bit in timing...the 10th of October period normally finds more bracken down as well as leaves...plus, while cooler is varying every year, dogs and I appreciate the odds of morning frost helping with moisture for sniffing.
Consider learning early successional cover and if WI has any such grouse production areas then that could be an option, tho a hard hit one. Woodcock will be where you find them, locals or migrants.
Play moisture, food and covert quality, ime.
Have fun in the quest for birds.
Words on the subject are abundant....from studies to literature.
Pick & enjoy.
A good gazeteer is nice ie Delorme.
Use a gps for pup and venturing away from a road...I've come upon and returned more than one lost dog in the Yoop....I have been twisted around myownself for a bit too.
Police for ticks!
Accept that wolves will likely not be much of a concern in October but, consider any critter that will be around and potential.
Personally, I find grouse do not require a daybreak arrival but....your option.
Not sure your gun choice but 20 & IC will be at any advised center with venturing away from that, quite common and ok.....pump, sem-auto, two-row or the perennial champ, the o/u.
Sounds like you will but every single dog has a degree of learning curve re game birds....especially a first trip of the year.
Allow both pup and you to have good days and less good days.....tailgate photos are over-rated.
Breathe deep and grin....take photos, make memories.
Good luck in finding what you wish.