telling him you want to redshirt is just negative effort. he will always say "your crazy" or something along those lines. But if he is still considering you even with the redshirt offered, you should be fine.
it's usually easier to do when you are not in a battle. i usually offer a few HVs and a few SVs (since scouting visits are effort that can't be refused) and 10 calls + 10 letters. that's probably overkill, but it's a mess when you offer it and then he stops considering you.
so if you have enough $$ and really want the guy, make sure you give enough effort that will counter the negative effort of redshirt. I have no idea how much negative effort it is, but I would guess something like negative 2 home visits??