You might want to ask if it is Co-Captains - that is pretty common in that type of operation. If it is then ask your friend if the other Captains are a good bunch and easy to get along with. If the answer is yes to both then no big deal dealing with the international stuff.

As far as the training for the aircraft find out exactly what they will pay for (budget) then contact Simuflite directly and talk to them about what you need and the cost.