It's possible, but there are still two more weeks of Challengers after this. If they think they need all 3 weeks then it's likely not going to happen.
It should also be pointed out that the top 11 in the race to Milan are all in the top 100 right now. So as you said, unlikely but could happen.
Yes. That would be more likely for the wildcard.
I guess my question stems from the fact that I couldn't care less about the format. They might as well make them play table tennis as far as I'm concerned. I wonder if any player feels the same and would dare turning it down to favor rest or ranking.
To answer the original question, to me Auger-Aliassime is the ultimate next gen not currently in at the moment. But that would mean a wide disparity in age and experience with the others, which might be a little odd. I would have gone with all players born in 1997 or later if it had been my choice, along with the actual rules.