I think you're reading this backwards. The "he" is Omar, who lived with his brother (Barack Sr.) when he (Omar) arrived in Cambridge. The previous sentence in context talks about Omar being three years older than the Sophomore boys in the prep school. So it's saying Omar initially lived with Barack Sr. when Omar arrived in Cambridge. Omar arrived in 1963 and Barack Sr. had already been there since September 1962.
...The only African student at the school, Obama stood out in a number of other respects. Not only was he three years older than most of the boys in the sophomore class, his arch colonial accent immediately marked him as different. That he initially lived with his brother in a rented apartment in Cambridge, a place often churning with visiting Kenyan students, added to his exoticism...
BUT I still would ask to see more to convince me he didn't arrive in the US until 1963. He was class of 1966 and to complete the usual 4 years of high school, he would have commenced in 1962.