I have bought up to Chairman's the last few years in early October. This gave me upgrade certificates immediately which I then used to book flights to Europe for me and my wife in envoy class. Come March 1 of the following year, I would receive another certificate and would book another Europe vacation for us. I thought this was a great deal but alas it is going away as I assumed it would. I still will receive my last certificates in a few weeks. I do have a chance this year to get to 75,000 miles but even if I do $2499 seems too steep a payment to buy up. Any ideas or strategies? The use of miles plus cash to upgrade on AA seems a little high although I will have over 1.5 million miles after the accounts merge.