Is it still possible to get a player whose WE drops when applying a redshirt to eventually get him to accept the redshirt with no WE drop? 

I know people had said in the past that if you keep taking the redshirt off and putting it back on, that eventually you can get the player to accept it with no WE penalty.  Or has this been fixed in one of the updates?

That loophole has supposedly been fixed.

I've pulled a redshirt and re-applied it once, and the WE dropped to 1.

if you pull it, it will go back - but the remove repeat loophole was fixed.  If he hates it the first time, he will hate it the nth time

Even worse than the first time