A properly thought out mild 383 can give you decent performance and mileage if you run an OD trans and rear end gears to take advantage of the 383's low and mid-range torque plus it will be mild mannered enough for your Mom to drive but still pull like a freight train when you mash the pedal. Concentrate on torque from an idle to 4500, that should put your peak HP somewhere between 5200 and 5500 and make for a fun driver that won't break the bank, should put you solidly in the 13's and it can run on 87 Octane. Put a set of 15 X 7 Ols rally wheels on it, paint the engine Corporate Blue and tell everybody it's a 305 or even a 267 and you've got yourself a sleeper
I'd recommend a set of Vortec heads, I talked to one guy with an '85 PU running a 9 to 1 383 with Vortec heads and the old 327/350HP cam who got 20 MPG on the Interstate on an 800 mile trip. He had a 700R4 with 2.56 gears and was running a 600 Edelbrock carb. That was his average mileage and on the return trip he had 700 Lbs. in the bed. A friend of mine rode with him and said it pulled really strong and they cruised right around 70 MPH. This is a full size pickup with the aerodynamics of a small house and is several hundred Lbs. heavier than your Cutlass.
There are several people at FullsizeChevy.com that are claiming an average of 20 MPG after swapping 383's into their full size trucks and they say the performance and pulling power is much better. Now most of these are EFI equipped and have OD but still that's impressive mileage.