Maximizing Mileage - Double Dipping

Chapter 1 - Shopping Portals
Chapter 2 - Dining Programs
Chapter 3 - Double Dipping

If you're as old as my father, you probably know what this photo is and why it's an appropriate reference for this post.

Earlier in this series, I told you how to get your parents to start earning extra miles from shopping online and from eating out. Now, we're going to discuss how to earn extra points from Double Dipping.

The Double Dip isn't really a new way to earn points as much as it is a way to maximize how you're earning. In the simplest terms, you earn points by buying a gift card to a retailer you were going to buy something from anyway. Then you go through your online Shopping Portal of choice and use the gift card to purchase your items.

Here's an example:

1. My mother wants to buy me an iPad mini for being such a great baby. Retail price is $329.99 at Best Buy.
2. She first goes to Walgreens to pick up a Best Buy few gift cards to cover $300 of the purchase and uses her Citi Thank You Preferred Visa because it gives 5 Thank You Points per $1 spent at a drugstore for the first 12 months. $300 in Best Buy gift cards = 6,000 Thank You Points worth at least $60 cash back.
3. She logs onto her Chase Ultimate Rewards Shopping Portal and searches for Best Buy. Chase is offering 1 extra Chase UR point for every $1 spent. So a $330 purchase would give her 330 extra Chase UR points.
4. Purchases the iPad mini using the $300 in gift cards and pays for the rest ($30 + tax) with her Starwood American Express. 
5. She selects the option to pick it up in-store. A few hours later she walks over to the neighborhood Best Buy and picks up my gift immediately.

So now my mother has earned 6,000 Citi Thank You Points, 330 Chase UR Points, and 30+ SPG Points. Had she just made the purchase directly in the store, she would have just earned 330+ SPG Points for using her American Express credit card. But by taking a few extra steps, she earned 6,360+ total points.

The biggest step is buying the End Retailer's (Best Buy) gift card from an Intermediary Retailer (Walgreens) that offers a credit card bonus. The best retailer bonuses are currently:

• The Office Supply Stores (Staples, Office Depot and OfficeMax) using the Chase Ink Bold or Ink Plus credit cards which give 5x Chase UR points
• Drugstores and Grocery Stores using the special Citi Thank You Preferred credit card which gives 5x Thank You Points (if you signed up using the special offer link) or the American Express Premier Rewards Gold  card which gives 2x Membership Reward points at Grocery Stores.
• Gas Stations using the Chase Ink cards (2x) or the American Express Premier Rewards Gold (2x).

If you're thinking this all the way through, this strategy has a lot of permutations as well. 

For example, when my father makes donations to his favorite non-profits/charities, he can just pay with his credit card and earn 1 point per dollar donated. 

Or, he could go to CVS and buy a $500 Prepaid Visa gift card for $504.95 (due to the $4.95 activation fee) and earn 2,525 Citi Thank You points upfront. Then he can slowly use the gift card over time to make the donations that he was going to make anyway. 

Yes, he spent an extra $4.95, but the 2,525 Citi TYP are worth at least $25.25, so he's coming out ahead.

Through this process of Double Dipping as well as regular gas/grocery/drugstore spending, my parents have earned about 90,000 Citi Thank You Points over the past few months - worth about $900. They COULD just use the points to lower their monthly Citi credit card bill, but where's the fun in that? Personally, I think they should redeem the points for $900 worth of Best Buy gift cards and get a few "free" iPad minis and start the Double Dipping cycle all over again.