Brandon, If your going to do allot of heavy towing I would definately do the twins or the 366 as a single. If your just towing light, like a bass boat or a utility trailer 8k lbs and under the S475 as a single will work great and also be easier on your bottom end. You can still town very heavy with the S475 as a single but you have to stay on your toes, watch egt's and have a good trans tune to keep rpms up. Its great for daily driving, light towing, playing on the street and drag racing, just not good for frequent heavy towing.
It really depends on tuning. A big single doesnt light until you up in the rpms which is better on your bottom end. Twins produce lots of bottom end torque which can bend rods easier. If tuned properly the power will come on more linear with twins and the bottom end will be fine. Lots of fuel down low and you'll have a hole in your block with twins.
x2 I love my s475, I was very surprised at how good it spools off the line. very minimal lag
Agree if you are not going to tow much. You can't beat a 475 single. Mine drives awesome on the street and makes good power.