Over the years I've had two diesel Chevys I repowered to 1st gen SBC's. Had the c30 dually for over 20 years. The M1008 I've probably had for 15 years. They weren't/aren't daily drivers, but got pretty regular use. I personally never cared about 24 volt systems or having dual alternators. These were work trucks for homeowner use! (firewood, plowing, material pu, etc)
As for wiring, not a show stopper. Pink Fuel solenoid wire becomes the Distributor power wire (at least for HEI/carb set-up) My C30 was a civvy version (obviously) so had less wiring concerns. My 1008 was a frame off restoration, so removed/modified wiring as needed for my use. Not hacked, but stripped down, cleaned up and re-loomed as needed. Bus bar now 12 volts, so makes a nice un-switched power distribution point!
Carb'd motor will be the easiest, but of course fuel injected provides better drivability.... Later generations SB's do provide more power potential, motor in my 08 is probably around 300 hp, so plenty for a work truck. (Mild cam, headers, carb/alum intake)
Both vehicles I retained the larger diesel radiator. Used appropriate sized exhaust adapters to join radiator hoses. Used the diesel trans convertor which was a non-issue!
Bottom line: It's not difficult and in my opinion is a upgrade. And, a carbed motor has very little troubleshooting required.... Fuel, spark, compression....
Once again, I drove these cucvs when they were new, allot! Hence, I have no love or allegiance for the 6.2!