One of the great things about Citibank is that their IT infrastructure seems to have been built in an age that did not allow for updates. What exactly does that mean? Well, theoretically, when applying for a credit card, Citi’s system should have real-time ability to assess whether or not you already have one of their cards, and if so, reject you from applying for the exact same card, with the exact same sign-up bonus. But because today is 2013, with the googles and interwebs, and Citi seems to be using Altvista and dial-up, the following is possible:

Yes, that is 2 Citi HHonors Signature Visa Cards. Yes, they both had a sign-up bonus of 50,000 points after $1,500 spend in 4 months. How did I sign-up for 2 of the exact same cards? I filled out one application form in Google Chrome and one in Mozilla Firefox, and then hit submit within seconds of one another.

Yes, that is over 103,000 Points (and Gold Status due to a sign-up bonus from last spring) – all for spending what I usually spend (rent, car payments, insurance, food, etc…). I’m pretty sure I am going to go for the Hilton AMEX Card that gives 40,000 Points after $750 in spend on my next churn in April. That would put me at about 150,000 Points. The AMEX Card will give me access to AXON Awards, which would give me discounts on 4-night stays in a hotel such as:

Hilton Bora Bora – 4-Night Stay: 145,000 Points with AXON Award
Hilton Maldives – 4-Night Stay: 145,000 Points with AXON Award
Add in that Liz will have 150,000 points as well within 60 days, I’m thinking a good use of those would be on our way to or way back from either Bora Bora or the Maldives in one of my favorite cities:

Hilton Phuket – 4-Night Stay: 85,000 Points with GLON Award
Throw in that my favorite custom-made suit store and panang-curry restaurant is within walking distance from the Hilton in Phuket, and I think this will be a trip-of-a-lifetime. 8 nights at some of the best hotels in the world, all free (including breakfast due to my Gold status). Stay tuned, and in a bit I’ll share how we are planning to fly Business Class for this trip. Total price-tag? A few hundred dollars for taxes.
UPDATE: After this trick working for years, there are rumors running around that Citi just fixed this. While I have not confirmed the rumors, if you have tried this and get a pending status for one of the cards, don’t call up the consideration number. Just let the system work its magic. Let this be a lesson, though, that when deals present themselves, there’s no time to think. Just act.
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