I have a lot of saddle time on the VT1100C, a very good friend has one. The Speedmaster will feel like a dream to you in the area of roll on power and leaning.
My friend prefers my America over his Sabre. The Sabre shaft to me is the only thing better. I prefer shaft to chain. Don't worry bout the air cooling, our bikes are not too hot for traffic. It won't cook you.