I guess one reason why to do that is simply to do something different and challenge yourself in the process. I love original big bolts- part of the truck driver still in me from way back I guess? I also love big bolts that are custom made to fit somebody's idea of cool and/or functional at a high level.
Chassis swap with bigger tires and wheels would look awfully neat and still have the flavor of the old big bolt but that's many a cold beer or glass of iced tea pondering session. Flipping the coin over and seeing the knowledge and expertise of this forum though, you might turn full circle back to an authentic ride.
I know this will be disdainful for some but my '30 Chevy 1.5 ton flatbed is getting new life with an updated drive train to include a Ford 9 inch rear and disc brake conversion on the front axle. (which happens to have had the smaller king pin axle of the lighter model trucks who knows why...). Plans are for it to be a 65-70 MPH capable daily driver/work truck/trailer puller.
I'm glad everyone does not modify like I personally prefer because I wouldn't be able to see and appreciate all the cool original stuff most of the other guys build.