OK, what size tire do I need to go to then? Or does it matter?
Depends on the rear tire. The 300's have a 1" tire size offset from the factory, a lot of guys, myself included run the same size front and rear.
So if your running a rear 24x9x11 which I think is stock? then you could move up to a 24x8x12 front, I doubt you'll find a 23" tire for a 12" rim very easily.
Or what I would recommend is changing the front and rear wheels to 12" (ITP Delta's are like $40/rim) then doing 25's or 24/25" or 25'26" or whatever you want really. But the 12" rims open up a lot of better tire options, and IMO increase the resale value down the road.
One other option would be to find take off rims (and tires too if that's what you want) off any 350 Rancher, or 420 SRA, Foreman, SRA, as they will all fit your machine and use 12" front rims, the foreman has 12' rear rims as well.