My advice: get a SO among your cohort in the Anderson-NUS program who has 1MM and 1K status and be their designated companion.
Otherwise you're probably better off Kayaking and looking for deals on cheap business class fares rather than trying to accrue status on United.
My impression is that JFK hubbed DL is better for credit card + flying your way to status, though their status (short of diamond) isn't worth as much as United's. (Again: just an impression, not sure).