KJ, I have flown through out Latin and South America without any problems. As long as you don't circle any place, the chances are quite good no one will shoot at you. The druggee's know that if you shoot at an aircraft, all that will happen is that much bigger ARMED aircraft will come and shorten their life spans. Corruption is a problem in some areas. That is why you have a handler. He is a local who knows which palms have to be lubricated.
As for risks shipping by container. Ships sink. No matter how tight you seal the container, moisture will enter so there will be corrosion. Ships are late. Containers get off loaded at the wrong port. And then when your container arrives you have to deal with customs to get it released.
About the only two countries I would have any concern about down that way are Mexico and Columbia. But with proper planning you can fly through each of them in a day.