I could find someone in between jobs to do it and the premium you place on overnight doesn't really reflect the world I know where I raised my family in Pennsylvania. In PA a great many decent good hardworking people have late shift jobs that don't get paid 10K a week and would probably like a side gig of something like this. There are a whole lot of people out there with night jobs or night shift with a ton of downtime like those working at hotels, security at offices and apartment buildings and warehouses who could easily manage setting up alerts with a contingency list:
1st priority: I prefer airports A, B & C
I will pay up to 200 per person to avoid connecting flights
2nd Priority: I prefer dates A, B & C
I will pay up to 100 extra to be next day
3rd Priority: I prefer hours x-z, a-c, l-m
I will not fly 9 pm or later so if it is 9pm or later go to the next day and see priorities 1 & 2
Extra night hotel, I prefer closer to the airport for convenience, please reserve me at hotels A, B or C if this process takes longer than 2 hours to resolve up to a cost of $X
As it was with us managing it the extra day cost us $1500 and a ton of aggravation. Room $800, rental car $150, Valet $60, car parked at home $60, plus all the meals for everyone and all the other stuff I needed to replace because I threw it out.