You want to do what's called corner pinning: basically, you "pin" four corners of a graphic or video clip to four points in a background clip, and then distort the pinned clip to match the perspective of the background. CS5 has a Corner Pin effect, but you'll have to keyframe it manually. If you have After Effects, you can do this a bit more automatically using tracking (either the built in tracker or Mocha), but the learning curve is going to be steeper. This effect shouldn't be too difficult to manually keyframe, so I'd try it out there, first.
From experience I think the only way is in AEFX. Using Trackers. (or MOCHA)
The truck movement will be far from linear so the tracking points will be all over the place and kind of 3D (2.5D)
I have tried manual tracking plus corner pin in PPRO. Its very difficult and results were never optimal.
I would love a basic Tracker in PPRO. (particularly for graphics / subject relationships). I would love invertable and featerable garbage mattes as well!
Yep. After Effects is the right tool for this job.
There's plenty of information on motion tracking here, including an overview and tutorials.
We can help on the After Effects forum.
The After Effects will do the tracking nicely for you.
If you have access to the book 'Adobe After Effects CS3 Classroom in a Book' (available online in the public libraries in Canada)
the tracking drill is very well explained on p.407 and is kind of similar to your project.