the 500 would be awesome in a '40. I built a 4x4 Studebaker truck with a 500 caddy in it. I sold the motor to a guy who's building a suburban. I had the 425 heads (which raise the compression on the 500 to 9ish:1) - he's building it instead of going diesel. I think he's right in his assessment - that the mileage will only be 25% less than a diesel but will have all the diesel torque. Those things are monsters stock, raise the compression, a decent intake (that doesn't make the air flow uphill), and some headers and 500/500/500 would be easily achievable (500ci, 500hp, 500tq). I even briefly considered using the 500 in my build - but then he came along and offered me enough money to send it to a new home.
I got into 500s because of an acquaintance that's been running them at Bonneville since the mid-70s (and setting records).
that said... a 396? you do like the less-favored power plants? it'd be a good cruiser motor because the small bore/long stroke - but shrouding would really limit its hp potential.