Are there any disadvantages to using a 9.5" wide rims and 285's on the front wheels? Or is it just rubbing?

 

With wide tires, you can pick up some self steering on bumpy or rutted roads.

 

Really like the direction you're taking this car with the hurst shifter, full length headers, windveil blue color, etc. Very old school. The wheels add a modern flair...edgy...and they fill up those wheel wells nicely from the side. It's interesting, though that even 285mm tires look slightly skinny from the back on this car. It may be the shape of the p-neros where the rubber meets the road. ie. a little rounded on the edges, instead of flat and planted looking. Not dissen your car mind you. Just think this car would look killer with a really wide tire in the back, but I'll bet your about at the limit.

As a side note, I lived in NE Ohio for most of my life and those row houses in the background are taking me back. Can't say I miss the white stuff, though.