While in most cases I'd opt for function over form, when we're talkin' about a Springer, well, it's a flippin' Springer! I don't care what front tire combo you use, it's gonna handle like a buckboard, and stop just about as well. I love my 07 for the old school look, which the 21 incher is a big part of. I did go with PM four piston brakes up front (replaced the rears too) just to give me a fighting chance with the cages. But if you want decent braking capabilities, don't look to a Springer, any of them.
For what it's worth I think the 09 model is pretty disappointing, the rear fender totally lost its classic "bobber" look, and as for tires, 200mm is enough, if the rear gets any wider it's gonna take on the look of every OCC wannbe luxo-chopper on the planet.
The Springer (any Springer) is a truly iconic bike, enjoy it for what it is, including its limitations. I'll take my Road King if I need to put on some serious miles.