318 to 390 stroker

What cam are you considering? Ultimately, what you care about is dynamic compression ratio to be low enough to stay away from detonation, not static CR, and the cam plus the static CR sets that. You have a heavy vehicle, so more care is typically needed for DCR.

You mention high stall and big cam so your DCR will tend to be lower with the big cam and you ought to push up the static CR as a consequence to avoid excess loss of low RPM torque. But that also depends on the use; the high stall TC hints that this is not a farm truck LOL. So what is the planned use and operation of this truck/engine?

Intended use for the truck is a very spirited cruiser. There might be some truck pulling and drag racing being done with it also. He doesnt really care how the street manners are as long as it's not completely ridiculous.

I guess the idea is that he's spending the money and if we can see a significant improvement by bumping up the compression ratio and running a bigger cam to get an overall better running truck when he gets on it is it worth it? Otherwise well probably just go with a milder cam and stick with the static of 9.6 or so.