1) First things first – get the Hilton HHonors Surpass® Card from American Express
It comes with a healthy, but not great, 60,000 points signup bonus after $3,000 in spend.
This card also earns with the following multiplicator:
Earn 6 Hilton HHonors Bonus Points for each dollar of eligible purchases at U.S. restaurants, at U.S. supermarkets, and at U.S. gas stations.
2) Find a supermarket that sells variable load Mastercard/ Visa Gift Cards. This Flyertalk thread details which card will work best.
I found a number of Safeways that sell the Metabank cards which seem to be the easiest cards to work with.
Find a cashier that lets you buy 2 or more Gift Cards with your Hilton Surpass card.
3) Find a Walmart near you that has a Money Center that issues Money Orders.
Most Walmarts in the San Francisco Bay Area claim there Money Order terminal is broken or can't be operated with a debit card. You will need to find one that works for you.
The gift cards you bought at Safeway will work as a debit card using a PIN.
Note that you should stay under $3,000 in purchases for every day (or 24 hours period) that you buy money orders from Walmart. Shoudl you exceed that Walmart may file a Suspicious Activity Report on you. While not an issue per-se it is a good idea to avoid that.
4) Take the Money Orders to your bank and deposit them. Make sure you deposit less than $10,000 in a single day.
Since Amex only closes the statement once a month and gives you time to pay your balance after that – you get the $1,000/day as a interest free loan for up to 45 days!
Ideally all 3 retail locations are close to where you live – let's assume they are and time/gas is negligible.
What is the cost of earning 6,000 points?
– 2x variable MasterCard Gift Cards $5.95 each
– 1x Walmart Money Order fee of $0.70
– no fee for the bank deposit
– no supermarket fees
= $12.50 for 6,000 points
If you spend more than $40,000 on your Hilton Surpass card Hilton will make you a Hilton Honors Diamond (otherwise you will earn it after 60 nights in a Hilton hotel).
Diamond status has a number of smaller benefits but notably you will get:
– lounge access
– free breakfast
– suite upgrades (many in Asia, less so anywhere else)
Since the 5th night is free on standard redemptions a 30 nights stay in a Category 1 hotel will cost you just $227.50. If you choose a hotel with a lounge breakfast, evening booze and evening appetizers will be included as well. Oh and did I mention you most likely will also be in a suite!
This is incredible value for any traveler!