Am I looking at the world schedule correct and seeing that if you get a recruit in recruiting phase 2 that you won't be able to redshirt him as the redshirt player deadline is before phase 2 even starts? I might also just be an idiot, could be that as well...

Thats the redshirt player deadline for the past season, you do not technically have to redshirt a player until that dealine, he just has to have not played a minute in a game for it to be allowed, this is used in stratigies such as redshirting seniors but waiting so they can practice before a huge WE drop from the redshirt. You can redshirt players that you sign in recruiting period two, I have done it.

Right, you can redshirt anytime leading up to the first game of the regular season. He can play in both exhibition games, and can still be redshirted. But then once a player gets any playing time in the regular season, the redshirting option for that player is removed.

Redshirting can be done if you go to the "Coaching" column on your main team page, then click on "Manage Roster".