Definitely possible.
Here's how I see May to IU playing out though, if it were to ever happen.
May has really good, sustained success at Michigan, if not great success.
IU moves on from Woodson next year, and hires someone else. For the love of God, the Admin picks a solid coach, and that coach has a very good 6-8 year run at IU. May is presently only 47-48 years old. He'd be in his mid 50s if the job were to open up again 6-8 years from now.
So, to recap...
Woody has a decent year next year, but we move on at years end.
We hire someone like Matta, or Pearl, and have a solid 6+ year run with them.
May is really good at Michigan during that time. But his heart is pulling him to IU.
When our next coach is ready to retire, or move on for whatever reason, we hire May.