I think it would help to know what your goal is. Says you live in MN. Are you trying to travel hack a simple 3 night trip to Colorado, or a two week grand tour through Europe? Personally, when I'm trying to use points and/or find insane deals on travel, I start with the flights. The Southwest card has an annual fee, but it can be well worth it if you're booking low point flights (typically very early morning flights, especially on Tuesdays or Wednesdays). For example, by signing up for the Southwest CC, you get 40,000-50,000 points after making the required transactions. If you book smart, this can easily get two people round trip nearly anywhere in the US from MN.