408 vs. 440: Which Would You Choose?

Demon Seed's car was a 383 with a 727 and it was an awesome looking car and a well put together package.
Seeing that you are starting with a blank canvas, i would go with a mild 10:1 440 with about 550 horses and the new Trick Flow aluminum heads.
Since we're spending your money, i would buy a S-60 Dana to put in the rear with 002 and 003 Super Stock springs, Schumacher headers, the Passon 5 speed trans, Centerforce clutch with an aftermarket ''blow proof'' bellhousing, big bolt pattern discs on the front with 1.04'' torsion bars, and topped off with an AAR six pack fiberglass hood. Subframe connectors and an upgraded cooling system are a must.
Then paint it black and install the Cragar SS wheels that you want. I would go with 15X8'' on the rear with 275-60 15s, and on the front 14X6'' with say a 225-70 14 tire.
This should easily get you into the mid 11s and be fun to drive with the looks you want.
Stroker small blocks are cool, but once you drive a big block in one of these cars, you will never go back, guaranteed..........
Boy it's fun spending other people's money!

I'm on the same page as this guy. 440 all day long.