If you want to do this efficiently without driving yourself and wife crazy, I would start by:
1. Discuss with your wife where and roughly when you want to travel.
2. Research which particular airline(s) will get you there most efficiently.
3. Research which card(s) give you the "biggest bang" on getting there for as free as possible and quickly.
The reason is: A lot of high, quick payoff cards have high annual fees. You want to "suck out"/use up the front load (the points they load on when you reach $2,000, $3,000, or whatever) and use them BEFORE the annual fee kicks in (such as Chase Sapphire). You want to dump the card before you have to pay the fee. In the case of SW airlines, you now have to pay $65 before you can "suck out" your front load points. If you fly SW a lot, it might be worth it (that's what I am currently doing. Last year I hacked a free flight to Vancouver and NY).