it depends on the class you want to pull in...and I dont mean weight.  What class restrictions are you talking about.  Can you run alcohol?  Turbos on a tractor that was originally naturally aspirated?  If both of these, then a 2255 on alcohol with a few turbos will walk ANY 1066s dog.  If you are talking close to stock, which I dont think you are because a 1066 cant make 1000hp anywhere near stock, Frank is on the right track with the Moline painted green.  A Moline 800 power unit on alcohol...or even PROPANE! with a turbo is a MONSTER! 
And that is with a relatively STOCK motor.  You can definitely do this.