It seems that there isn't room in the pouch for two older joeys. According to this link, roo twins are very rare and if born in the wild, the weaker will generally die. http://www.abc.net.au/local/phot... However, kangaroos can have two or more joeys of different developmental stages 'on the go' at once. read more
As you can see from these photos, kangaroos can have twins but it is a very rare sight because a mother simply cannot carry 2 developing joeys to full size. Unfortunately one joey has to leave the pouch which must be the most horrible situation for all concerned. (These are Eastern Greys). read more
However, kangaroos can have two or more joeys of different developmental stages 'on the go' at once. 'Kangaroos usually have one young annually. The joey remains in the pouch for nine months and continues to suckle until twelve to seventeen months of age. Kangaroos can have 3 babies at one time. read more