I am working on a 59 fleet option gmc half ton. I have always wanted a straight axle 55 two door, but I dont have the room with all the other projects I have so I am going to build a gasser style truck. I am building a 283 with vortec heads, a weiand 144 supercharger and a big doug herbert hydraulic roller cam mated to a muncie 4 speed. wheel vinteques gasser wheels up front and chrome steel wheels out back. my front fenders are rotten so I am replacing them with fiberglass fenders and keeping the single headlights.
I don't intend to dis your plan at all, but when you said gasser style for your 59, I immediately pictured a blown 292 with zoomies. Which I think would also be cool.
honestly i really wanted to build a blown 302 jimmy, but after a lead on an engine fell through and after pricing parts to supercharge my 270 I just figured it would be cheaper to go with the 283 that i have just laying around in my way. I will keep the 270 and might do something with it later.