Similar story... I wanted to take my daughter on a western hunt this fall as she's a senior and we wanted some dedicated daddy/daughter time. She was young enough to apply for a youth elk tag in WY and got the tag.
A good friend of a friend had hunted elk in CO 6 times (killed a cow his first trip) and killed 2 antelope in WY. His son went with him on the antelope hunts and was also interested in a youth cow tag. He also got the tag.
Both of the kids are experienced whitetail, upland, and small game hunters.
I'd been on one wilderness elk hunt last fall.
Logistically, since he had the most experience and had a contact in Gillette to help us with locations, information, tips, I gladly offered to drive. Since this was a mid-October hunt, we brought tents/camping gear to hopefully spike out for a couple days, but also realized the kids' enjoyment was paramount. With this in mind, we rented a forest service cabin ($35/night) with wood stove, bunk beds, and outhouse as our primary base camp. This ensured we had a warm place to land every day as well as an efficient means to dry out clothes, etc...
We both brought frozen meals prepared at home for dinners every night. For lunches we got our own groceries and also shared leftovers. He brought a 2 burner propane stove and I brought one of my full tanks.
We waited until the end of the trip to settle up on gas money vs. cabin rental. As it turned out he owed me around $50 for fuel. No biggy...
We didn't punch any tags on the trip, but we learned a lot more about each other, and the shared suffering in the mountains galvanized our friendship. He's no longer a good friend of a friend. I now consider him one of my best friends. Our kids also bonded, and I'm sure will be retelling the stories of the hunt whenever they see each other in the future. Although we didn't kill anything, the hunt was still an overwhelming success.
Like others have said, preparation is key, and if you have any doubts about any of the guys pulling their weight, its best to have those conversations before any tags or other money is spent. Woodsmanship, marksmanship, etc..., won't make any difference if you don't have shared committment, positive attitude, and expectations for the trip. Good luck!