You would need to do this in multiple package with selection criteria to create the order in which they get delivered.. Package builder does not order the delivery of files, so the exe you need first would have to be the first package..
Is there a detailed example of such a complex build?
This is as close as i think we will get with how to use properties.
Basically all you are doing is in the first package have no criteria, all devices get this. add a property to the first package that says something like, custom.package = 1
on your second package, when you are creating it you know want to single out only devices that received the first package. so you would a selection criteria of custom.package = 1 and now another property in the ini of custom.package = 2
on the third package you would know use the property from package 2, custom.package = 2
Repeat this process until you are done..