IMO you're making a mistake. The small increase in hp and tq won't be noticed when you give up the 4. 44 or 4. 88 gears and the softer suspension and smaller brakes of the pickup won't do as good a job when hauling your trailer.
If you run empty all the time, yes, you'll be able to feel and appreciate the faster acceleration provided by the hp and tq of the new pickup and the smoothness of the new chassis. I'm sure the ride and interior features will be much nicer on a new 2011.
small increase? 305 hp vs 350 hp = 15%
4. 44 gears vs 4. 10 = 8%
4. 88 gears vs 4. 10 = 19%
the thing about gearing is that you may be better off with the 4. 88 for towing in 6th or you may be better off with 4. 10's and letting the trans grab 5th or 4 th and having the od for the flat ground and get better mpg. it really comes down to the tw of the truck and trailer and that trailer at 14/15k doesn't really warrant a 5500 truck. if you were say pulling a 25 gvw trailer day in day out, yes get the 5500.
the truck will be lighter = less to push around and more mpg's
Your math makes good sense in a theoretical application.
But what percentage of the time does a driver use full throttle and high rpm? Our Cummins engines don't produce maximum hp until 2900 rpm in the C&C and just over 3000 in the pickup application.
Under normal driving using part throttle the driver never reaches maximum hp so how will he derive any advantage from another 45hp?
If you take the calculations another step and include the cost of trading an '08 for a '10 model I wonder what he'll pay in dollars per (theoretical) hp gain. I would estimate approximately $300/hp.