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Eastbay1K, I feel like I did most things right with regard to taking full advantage of select mileage programs. I've had a great run.
In 1980, while Denver based, I purchased a lifetime membership in Continental's Presidents Club for $300. While United subsequently converted it into a lifetime United Club membership, it's essentially useless since it's only good if I'm actually flying on United, which I rarely if ever do since moving to Alaska in 1988.
What I wish I'd done in 1984 is to have paid the $700 asking price for Alaska's Boardroom when it became available. At the time, it looked way overpriced given that Alaska operated only four lounges, and at that time I couldn't see over the horizon to the airline - and its lounge network with AA - growing to the extent that it has. As a result, I've paid out thousands to maintain my yearly membership in the Alaska Lounge over the years.
But it's cool. On the whole, Alaska ha been berry berry good to mee!