Originally Posted by ehallison

Addressing only the credit card aspect of which card to use for your stays: If you truly value each currency as you have shown in your calculations, then it's not rational to use the Citi Hilton card. Your own calculations show that you'll effectively earn 3% on that card, 5.4% on the SPG card, and 6.6% on the Chase card. So you'll need to ask yourself "Do I really want to earn Hilton points worth 3 cents for this payment, or Chase points worth 6.6 cents in Hyatt (or whatever program) transfers for this payment?" The math for SPG card is obviously a closer call. But I wouldn't choose the Citi Hilton card for payment in your circumstances, especially as you mentioned you already have a stockpile.