A flathead with all those goodies just screams to be showcased in a nice roadster! My first car was a 47 Mercury convertible with all the leftover parts from the family dirt tracker, a 34 3-window coupe. Offenhauser heads, headers, dual exhausts, mild cam, and a few other go-fast options. I chose to do most of the internal engine modifications like a 4" stroker, 80 overbore, porting/polishing, etc., but I stayed with a slightly oversized single 2 barrel carb. (55 Ford 272) The car had awesome low end torque because I didn't over-carburete it. If you're running the Hillborn and you do decide to put the engine in a stovebolt, find a really low rear end gear and keep the engine wound up. The truck will probably be too heavy to take advantage of the performance potential of the engine.
Flatheads ran rings around stovebolts when they were new, and some things never change. You just need to let the engine wind up, and keep it cool. There's a reason the valves are hard to adjust- - - -once they're right, they never need another adjustment for the life of the engine!
Jerry