Repower, but run, do not walk away from the Detroit unless you're willing to swap the entire running gear, including the front axle and springs to handle the extra weight of the Diesel engine. A 4-53 would be about the biggest Detroit you can fit comfortably into that engine compartment, which would probably have less usable torque than the 292 and like most Detroits, it would have to be run up against the governor all the time to make enough power to get out of its own way.
If you're swapping engines and you want mores power, there are plenty of 454's available that will make more power than the 292 without re-engineering the entire gear train as well.
Jerry