Based on similar cams I've used in 406" SB & 446" RB street cars, either should be fine for that application, and the larger of the two will easily be absorbed by 440".
Lift (within reason) is kind of "free power", meaning it doesn't typically have the low-RPM laziness side-effect that too much duration gives.
Limiting factor to some extent is the manifolds, but for this kind of application I wouldn't lose a minute's sleep over it.
I'd stick with a fairly tight converter with that gear & weight & usage, pretty much stock; did that with the 406 car (Duster, AC, 3.21 gear, 28" tire) and it was very responsive in street driving, pulled 17MPG.
I'd also in that application lean toward a Thermoquad unless you have the budget & desire for EFI.
9.5 with Stealths @ 6700 feet is plenty safe even with those fairly small cams, which tend to give good dynamic CR.

Agree on photos, love the fin cars; 1st car I ever drove (age 12) was the parents' '57 Sport Suburban (which had a 383 swap).