Congratulations on the new classic truck gig. I've always liked your articles and followed your writing since you had that '57 Ranchero with the Desoto grille. (Still can't look at a Ranchero without picturing that grille choice.)
Your '57 Chevy project is a great choice-a favorite year, especially with the unique grille and the one-year-only ribbed hood, similar to the '57 cars. The small-window cab is certainly what most people can afford, with the Big-Window becoming pricey.
You said you'd like to tow with the truck, and that gave me the idea of perhaps a theme. I'd consider modeling it after the '50s push trucks we see in all the old shots of drags and Bonneville events. Build it beefy; perhaps even consider using 3/4-ton suspension and still keeping it relatively low. Along that theme, I'd get out the various tube benders available and bend up some unique front push bars, rear nerfs, perhaps even try and duplicate the floating grille in tubing. I've always thought that replacing the Stepside rails with larger diameter tubing would look sharp, and even radiusing the corners so they flow around the front of the bed seamlessly. If you ran the tubing completely around the bed, perhaps you could create a tailgate that flowed out of the tube.
Carrying the theme a little further, replacing the hood ribs with larger tubing would add some brawn to the look. I look at all the different ways the '57 car hoods have been modified, and it should work as well to the truck. For the cab, look to the '88-99 Chevys for cab lights with clear lenses, they're fairly low profile and don't require much for installation. The interior of these trucks is great to begin with, so not much is needed except air/heat and stereo (for talk radio).
I'm a fan of the suede/flat black look, with more of a satin appearance. DuPont hot rod black looks good. I'd look to accent the satin with certain areas in gloss, like the cab roof. I've seen eight-lug reversed wheels advertised, and if you got them in chrome with large baby moons the look would certainly confuse folks.
Finally the engine choice I'd make is the W motor, with a healthy 409 mated to the TH400. Hey, they always called them truck motors, right?
Good luck with your project. Look forward to seeing how it comes out.
Thanks for your suggestions. I hadn't given any thought to the push truck theme and it's definitely worth consideration. The towing I'd mentioned is nothing really heavy-duty just your typical camper trailer so I don't foresee having to upgrade to overly stout suspension. The body mods you suggest are a definite possibility. I'd originally planned on just repairing the small bit of rust and trying to get the sheetmetal straight enough that it doesn't become the friendliest truck in town (waving at everyone as it goes by, if ya catch my drift). Unfortunately the truck came with a '55 hood so it's smooth rather than having the hood ribs like the '57 version-though, I guess I could modify it using the larger diameter tubing you spoke of. The push/nerf bars may well be incorporated too, that'd go a long way in achieving the push truck look you suggest. The W motor is another neat idea, but I think because of budget constraints I'll be sticking to a small-block/TH400/9-inch combo. Anyway, thanks again for the ideas. I appreciate the input. Who knows, you may well see the push truck theme come to fruition!