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I need help understanding United's upgrades and upgradeable fares

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Okay...we are trying to get from ORD to HNL on United in Septebmer 2009 (actually trying to get to LIH, but figured out that it appears to be making the most sense to just book the HNL to LIH leg on Hawaiian Air - that will be another post!).

I have found an "S" class upgradeable airfare that appears reasonably priced (though slightly more than the fare that is not upgradeable). We want to ugrade. A couple questions:

1. All over the place in red, UAL states that there is no guarantee that upgraded seats will be available. Of course we don't want to pay an extra dime for the "upgradeable" fare if we actually can't upgrade. When I called United, they said I would need to actually book the fare and contact Mileage Plus to find out if there would be upgradeable seats available. They did confirm that there are first class seats avaible, but not all are available for upgrade.

2.The new upgrade chart (effective July 1, 2009) shows that the ugrade will cost 17,500 each way PLUS $250 to $500 per leg. How do I find out the exact cost. I think it may be worth it for an additional $500 per ticket, but not $1,000 (still actually debating on the $500).

3. In the past, I have first class with miles and got screwed by United when the flight got cancelled in advance of our trip (usually months in advance) and we got put on another flight and told no first class seats were available. Only choice was to go coach (despite the fact we used enough FF miles for first) or to cancel. With the upgrades and high dollar cost associated with them, any clue on what the odds are that this could happen?

Thanks. I really hate United sometimes (despite being a PE, I rarely use my miles becasue I find it to be a pain in the butt!). Appreciate the input.

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