re: Blue Sky American Express Card

the Diesel is right. You need to pay it yourself first.

Example: I'm going to Biloxi for Memorial Day weekend (don't judge). I will use my credit card for the expenses and pay my month-end bill like I normally would on June 2nd. Some time in mid-June, I'll be able to log in and redeem my points for those expenses and get the $900 bucks I spent credited to my account balance. That'll take a load off of my June payment.

It's a bit tedious, but I'm used to it. At least you have 100% freedom to purchase travel through any vendor with Blue Sky. Many cards that allow you to pay with points up front also make you book through their travel services. It can be limiting, especially if you can find your own deals.