Propably you have bug with synchronization your local region with region on the ea servers. Check this out: http://answers.ea.com/t5/Miscellaneous-Issues/Synchronization-problem-in-Region/m-p/1078558#M73517
What you need to try is: delete SimCityUserData folder in Simcity and restart game. Altough you have to be prepared to loose your progress.
From the city your sending it from go to region view and watch the vehicle and once you see it enter the city your gifting to then it is safe to switch city do the dame from the city that is receiving the money .