Some players will never take it, some will take it but it takes multiple tries and others take it the first time. If you inform them of redshirt during recruiting you got to throw out extra effort such as visits or he'll stop considering you. If they don't take it without the inform of redshirt when they show up you can just take it off no harm done and the WE loss goes right back to normal. WE is very important in this game, so I'd remove the redshirt to re-gain his WE.
I thought Dan said you weren't moving up? Anyways, if you got any other questions site mail me or Dan - he sucks though.