Ah, if you want the wings to be evaluated more than once then you can try simply switching the second event to a repeated when rather than every-time. It also explains why you did things in such an odd fashion in the first place.
To use random-of or random-multiple-of you use them like this.
Wing
-->every-time-argument
---->Random-Multiple-Of
------>1
------>2
------>3
------>4
------>5
------>6
------>7
---->=
------>wing(0)
------>0
-->modify-variable
---->wing(0)
----> <Argument>
-->modify-variable
---->delay(0) (this is for delay in arrival between wings)
---->mission-time
-->Invalidate-Argument
That won't work for what you're actually trying as it would remove each wing from the event as it was used up. You might be able to get away with changing that by adding the numbers 1-7 in a second time but I've not tried duplicating an argument before so I've got no idea if it would work.
For something like this you must use random-multiple-of. The difference is like the rand/rand-multiple SEXPs, random-of evaluates at the start of the mission and will always call the same argument. You use it for events where for instance you wanted to pick a random ship at the start of a mission but wanted the event to repeat using the same ship for the rest of the mission.