I have an addictive personality, so it didn't take long for the whole miles and points game to become just that. I kept spreadsheets. I pored over every miles and points forum I could find. Eventually, I got into the dollar coin scheme, which I wrote about for Pacific Standard in 2013:Everything is worth the money if you're using someone else's
I would order $3,000 in dollar coins (the maximum allowed) from the U.S. Mint and charge the purchase to my Starwoods American Express credit card. Then, the Mint would ship them to me for free, and I would deposit the coins into my bank account and pay off the purchase with the currency value of the coins. (The coins came rolled from the Mint, and my bank accepted them rolled, so there was no effort on my part in the turnaround.) The whole cycle would only cost me the time it took to bring the coins to the bank. Rinse, repeat, etc.