It might be better to put this spend on American Express Gold because 4 Membership Rewards points converts to 8 Honors points, with the flexibility to transfer to many other programs.
Thats a great idea, I hadn't really thought about that. I was going to do in chunks. 1k a month for monthly student payment amount, then my employer gives me 20k once a year (15k after tax) that I was going to put towards loans. Maybe I will break that up into smaller purchases. I hadn't really thought about getting flagged by AMEX. Maybe i can spread it across multiple cards, get one in my wifes name as well as mine. What do you think is reasonable spend at a grocery store? 3k?