I come in peace....
You have to wait until the end of your career to apply for a 6th year, because you have no remaining redshirt years to use.
A normal medical redshirt request is processed any time because you just change a year you participated in and got hurt to a redshirt year that you still have available.
There is a 0.1% chance he gets an extra year in this case, as the only things outside of injuries that ever get granted is when a player has to leave early in the season due to family issues, and those are rare. Even in cases where the player gets hurt early in the season and misses the whole year, they deny medical redshirts if the player participated in any practices for the remainder of the year and was released by a doctor (see ULM's running back that was denied at the beginning of the season even after participating in fall camp).
Your new basketball court is really cool by the way.