This is the simplest strategy for earning and redeeming points for $1,500 of travel each year. The way you are going to earn that is by simply opening two credit cards that have good sign up bonuses. You can even use your vacation spending towards the minimum spend on the card! Here's more on how to do that:

If you have a partner, you could each open one card and use your points together or separately for two different vacations.

If I were going to do this, I'd start with Capital One Venture Rewards Credit Card. It's better to start with the Capital One Venture (annnual fee $95) than Capital One Venture X Rewards Credit Card (annual fee $395) because of some eligibility rules Capital One has.

Your Process Might Look Like This

Jill opens a Venture card (using Katie's affiliate link). She spends $4,000 in three months and earns a 75,000 point bonus. She then also uses the card to sign up for TSA PreCheck for free.

Jill refers Jack to the Venture card as well. She gets 20,000 points for referring him. He earns his own 75,000 point bonus. He also uses his TSA PreCheck credit to get that for himself.

Jack and Jill book a vacation using their Venture cards. Then they use their points to cover the travel purchases. They spent $95 each on annual fees. But they earned a total of 186,000 points! Redeemed for travel purchases, that will give them $1,860 off their vacation!

The following year they could each get the Chase Sapphire Preferred® Card and earn a similar amount towards travel.