I was strongly considering this but since I'm going to be outsourcing most of the development I was thinking about how difficult/feasible it would be to do more

I was strongly considering this but since I'm going to be outsourcing most of the development I was thinking about how difficult/feasible it would be to do more or less 4 versions of the app. (2 free but restricted/ad supported for each platform AND 2 full featured versions for each platform)....