Guessing here
I'm guessing it's an Alpha 1 Gen 2 outdrive, this was quite common on the 4.3s (I have one for example). If it's a carb job (2 bbl or 4) it should have a cutout switch on the throttle bracket that temporarily kills the engine when shifting into gear, it is more pronounced when shifting into reverse on mine for some reason. IIRC, the switch kills ignition for a second to avoid gear clash on shifts (primitive but it works). Check to make sure this switch actuates, it sounds like yours might be getting stuck during the shift and killing the engine.
The switch should be located on the shift side of the carb (opposite the throttle actuator), on my 4 bbl it's on the left side of the carb as you face the engine. Switch is fairly cheap, should be able to find it online. If you're EFI, it should still have the switch somewhere near the shift plate.
Post how this works out for you.
Oh ya, replace the steering cable if it's sticky...they never get better no matter how you lube them, same goes for throttle cables.
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