Wow, you guys are impressive. I'm certainly looking forward to installment #2!
My answers:
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How was the value for the money paid in 2009
I think there's two ways to answer this question.
From a purely emotional standpoint, I paid for an experience, and I was blown away. It was unique. I still can't get over how much we've done and how much fun it was. Even my friends who aren't geeks have been stunned by my stories and pictures. I spent a lot (doing the whole deal from ORD, going C all the way, going for the expensive room at Seeheim etc.) and it was 100% worth it.
From a purely financial standpoint, the value wasn't always consistent. The TATL C fare was a huge deal. I wouldn't bother upgrading if I could buy such Z fares when I fly on my own. The upgrade to F on the way back (despite it not being allowed in theory, but many of us did it anyway) sealed the deal. The charter in C, again from a purely financial standpoint, was a bit less of a value -- it was significantly more expensive than Y but at the end of the day, due to issues with logistics and time, you guys weren't completely able to deliver the amazing service you had envisioned. It was cool to be at the front of the aircraft, though. The hotel in FRA wasn't very cheap, especially considering we hardly had any time to sleep

One thing to keep in mind though is that we got fed all along for free -- our individual meal budget was a solid $0. It's easy to look at the expenses and overlook that fact. Finally, my UA fare going to ORD was a bit steep simply because I held on purchasing until the last minute, because UA flip-flopped a little bit and at first LH wasn't willing to ticket disconnected segments. If next time around we can know some fare details a bit ahead of time these costs can go down.
At the end of the day, the value obviously was great, especially imho for those folks that flew Y. There's just a couple details that could have been optimized to make it an ever more awesome value.
How many days can you be away to participate in a DO
This is a tough one. Anything more than 1 week probably won't be an option. 3 work days + 1 weekend would be great. Obviously this may not be enough for a RTW. At the end of the day, the earlier I get firm dates, the more likely it is I can make anything work. Over 1.5 weeks is a no-go, though.
How much money will you be willing to spend
Anything. Sounds stupid to say, but I'd eat pasta for a year to make it happen. Heck, I'd buy a F RTW fare without thinking about it twice.
Random suggestions:
- Boeing (already suggested.)
- Visit the main UAL command/control center in Arlington.
- An A380 leg on SG (if we do the RTW.)
- Accomodate for 3.5 hr of sleep per night instead of 2.5

- Try as much as possible to announce firm dates as early as possible even if the program details aren't completely known.