I've never attempted to mileage upgrade a CO flight before so this is all very new to me. I'm flying CO #667 from IAH-SEA-ANC at the beginning of July. The one-way upgrade should set me back 15,000 miles with no co-pay. As of now, continental.com tells me that I can't confirm space in first, but that I'll be added to the waitlist. A few questions:

(1) Does CO view IAH-SEA and SEA-ANC as separate segments for purposes of clearing the waitlist or will they clear together? Stated differently, if upgrade inventory ultimately opens up on IAH-SEA, but not on SEA-ANC, will I be upgraded on the former, while kept on the waitlist for the latter (or vice versa), at the full cost of 15,000 miles? Is there any way to request an upgrade only if both legs are going to clear? Is it possible that one of the segments might be available for upgrading now while the other is not, or would continental.com tell me so if that was the case?

(2) Is there any way to monitor the waitlist with ExpertFlyer, KVS, or some other tool? From what bucket does the mileage upgrade inventory pull?

(3) From a strategic standpoint, should I request the upgrade now? Monitor things until closer to the date of travel? I suppose it's possible (albeit, perhaps overly optimistic to think) that CO and UA may have reciprocal complimentary elite upgrades in place by the beginning of July, at which case, I might be able to get upgraded without paying any miles. I assume downgrading myself between now and then, if and when upgrade, should that scenario play out is not an option, right?

(4) Is my understanding that the waitlist should clear behind paid first class tickets and Y/B/M-ups, but before any complimentary elite upgrades are doled out, correct?

(5) Why does continental.com offer me two options, "Upgrade Individual Flights," with both the outbound and the return separately listed at 15,000 miles each (which, I'm pretty sure, is correct) and "Upgrade Entire Trip | 15,000 miles" (which is both incorrect and misleading)?