original cars are worth more than modified cars generally ... although if the car is just a regular GP (not SJ or other rare model) - the value isn't hurt too much by swapping the trans, especially if you keep the original one and sell it with the car when you do sell the car.
It also depends on the type of driving you do a lot of - if you are mainly on back roads, under 50 mph, then I would keep the original trans - if you do a lot of highway driving - then the overdrive would be nice for ride comfort(noise) and mileage - along with wear and tear on engine.
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1969 Judge, 4-speed, CR/Parchment, Quasi-Survivor, #'s match - under restoration
76 Cutlass Salon, 54,000 original miles.
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