This is where you lost me Kalle. A short wing has at least a 20 yard head start from his deep partner. And on punts, it's closer to 50. In my opinion, there's no reason he should be passed by the deep official. Assuming a clear sideline and you don't have player traffic in front of you, letting the deep wing catch you is a pretty good indication that you are not doing what you're supposed to be doing.
I was thinking of a situation where we have a 90 yard uncontested interception return after a short pass, and the short wing being slower than the deep wing. I'm not really sure how good each of the incorrect options are in that case.