Excellent adventure, or bogus journey?

Our trip to the UK approaches. Panic sets in. Here’s the story.
Regular plane tickets cost way too much. Slightly more than gallon of gas, at around $1000 a piece. No way could we afford that. I have a friend who works for an airline and can get us “friends and family” passes for way, way cheaper. The catch is, you’re basically flying standby, so there’s no guarantee you’ll get on.
As I was confirming everything with him yesterday, he noted that the loads look “doable, but iffy”, meaning we may get stranded in Chicago if there’s not room on the flight. We would have to wait until a flight came up that did have seats.
As another kink, his airline has an embargo for certain dates during which friends, family, and leeches can not fly without the actual employee being present. So he’s going to have to “bid” for his days off and hope he can get our departure date off so that he can fly to London and then fly back with us (we will, of course, pay for his even more greatly discounted ticket back and still come out at less than half retail price). Should he not be able to get those days off, we would have to buy tickets from London to Paris, and fly out from there, because the embargo is only on westbound flights from London and Amsterdam at that point. You following? Probably not, but that’s alright.
I am still looking forward to this adventure, but hope we end up as Wyld Stallyns, and we don’t end up playing twister with death. (movie references in case anyone was confused)