Jesus is slightly wrong.
You and the truck are travelling at 40MPH...therefore, when you jump up...the lorry has more momentum than you, so you will move back a small amount. So yes, the higher you jump, the further forward the truck will go.
Yes, wind resistance is also a major factor.
Your outcome is correct but its not exactly to do with a difference in momentum.
Air resistance and mechanical friction are slowing the person and the truck down, but the trucks engine keeps them going at 40.
The jumper is outside the truck (on the flatbed trailer) so he will experience alot of air resistance just like the truck.
So long as he holds on to the truck, he will get enough propulsion from the truck (which is driving at 40mph), to maintain 40mph.
Once the person jumps, he is no longer being pulled forwards by the truck, but he still has the same amount of air resistance trying to slow him down.
The truck has its own means of propulsion so keeps driving happily at 40 as the jumper decelerates. Its momentum is irrelevent because its not changing speed.
Even if it did lose propulsion, theres no reason to say the truck would decelerate less than the person.
Of course the truck has much more inertia 'trying' to maintain its speed, but it also has alot more air resistance, and mechanical friction slowing it down, where as the man just has air resistance.
Also it depends where he stands on the truck how much air resistance he feels.
And In any case, we shouldnt be driving flatbed trucks...
By the looks of the first picture, it wont be long before our nasty carbon footprints start affecting the climate on Antares.
Think of the poor little Antares creatures... im welling up..