Hunter, I've gone through a couple of sets of saddle bags. This past year my wife bought me a matching set of insulated horn and saddle bags by Trail Max in Montana. I usually pack food items and other smaller things in the horn bags. The large saddle bags will carry a lot of drinks. In addition to "adult" beverages we also freeze bottled water to keep everything cool. This works great even on the hottest of days. I like the look and feel of leather saddle bags as well. Leather can also be a good insulator especially with the frozen water bottles.
The Black Hills are indeed a great place to ride. We have hundreds of miles of trails with all kinds of experiences. We prefer a place called Hay Creek Ranch between Nemo and Deadwood in the northern Black Hills. This part of the range is quite similar to the Rockies terrain and vegetation-wise. You could ride for days exploring mountain tops, creeks, caves, and alpine meadows. It is a great place to get away from the cares of the world.
Another tradition of mine is to be an outrider in the Days of 76 rodeo parade in Deadwood each summer. As you may know, it is common to have entertainers between rodeo events. One of the "shows" at the 76 is a stagecoach robbery. One of my good friends is in charge of the stagecoach robbery. He asked me to help him with this several years ago. This was two days before the rodeo started. We worked together to break one of my horses to gunfire, and I went up to help.
After the first performance the main stagecoach robber wasn't able to perform, so I ended up being the main robber. Needless to say, I was hooked. I now regularly play the part of the robber, but this year I was the good guy. It is a blast. It combines horses and guns...two of my favorite things!
You can see video on YouTube by searching Days of 76 stagecoach robbery.