I dont have any help for your delima as i'm somewhat in the same shape. I carry only 5 keys though.
I do have a few additional questions.
1st Is there a universal key fob out there that is not HUGE. I dont know who designed chryslers fobs but they are too darned big.
2nd Is there any reason not to trim down and redrill new holes in the keys? I meanis it really necessary to have a Truck/Car key with a 1" x 1" black head on it?