I just helped a friend stuff about 500 horsey goodie bag last week before a big endurance race here.
She sells equine supplements as a side job and hands out product samples, flyers & coupons for all sorts of equine stuff at horse shows and events. Each plastic bag had about 6 different flyers/inserts, for supplements, tack, etc. we then added plastic mane and tail combs with hoof picks and salt and mineral supplements. You started with the large papers first, topped them off with the smaller flyers and inserts, added the supplement samples and combs last.
We started together but I decided that her making the contents piles and me stuffing the bags was a better and more efficient production line. Took about 3 hours, man, it was tedious. haha