Chavez's money can buy him a lot of hardware but he wants but he needs properly trained and motivated people to use it. The US didn't get as proficient as it is by using all its capital on hardware.
Can you say "volunteer Cuban pilots and ground mechanics"? And they won't be lacking for aviation fuel. Although a Venezuelan engineer I know (works in the US) says the refineries in Venezuela are about to break down due to lack of maintenance (his family used to work for the state oil firm until they protested Chavez one too many times).