[oostevo]

That sounds awesome, but I'm a little skeptical. The app would have run a huge optimization problem over your schedule and preferences (how would it know that you had a friend that could drive you?) and the airline reservation systems (which don't exactly have a well documented API, even internally).

For now, at least, this sounds like a problem where human involvement is really useful.

Cranky Concierge, as someone mentioned below, is one great option.

Another is paying the ~$50 for lounge access for the day, to talk to the reservations agent at the desk inside the lounge. They're usually much more experienced, much more likely to spend the time to do creative routings, and haven't just had to deal with possibly several hundred angry passengers. In one case with United, I stepped out of line to speak to the gate agent after my flight was delayed several hours and paid to go in the lounge. I wound up getting the last confirmed seat on the next flight, whereas the person just in front of me in line had to go on the standby list (which she didn't clear). That $50 was _well_ worth it.