For one thing, isn't the Hilton AMEX a $3000 spend? It's $750 to hit the first threshold (40K), then $3000 TOTAL to hit the 2nd. And you have 6 months to hit that higher limit. Go slow, $500 a month will be fine. I hit $1000 in a week (legitimate spending) and will cool it down to less than $1000/month from here out (mostly because I have other spend).