I would do 440/727, I never did it but seen it done. I would definitely first try to free up the 383, if its not full of rodents and doesn't have a rod hanging out of the block, she probably runs good.
One of the cars I regret most for getting rid of, was a 59 sport fury (Not a touch of rust, had some dents, and no headlights), but the car was kept inside for 30 years, had 24K miles on it, 395 golden commando, I found lights for it, I did the body work ALL HAMMER AND LEAD! Painted it, sent out all the chrome ($800 back then lol), the car looked great.
My point is though, the motor was locked up solid, I yanked the intake and it had a bit of rodent residue but nothing crazy, I drained the oil and it was all oil, I filled it with marvel, every hole I could get it into, I even pumped it through the cooling system.
After a little time I went over and gave it a try, broke it free with a bar, then turned it with the starter, washed it out, put a good carb on, plugs n wires, full of gas oil and 12volts, and she started right up, I mean like it was never shut off. It smoked for 15 minutes and man did it run good, tranny leaked a bit at first but even that stopped, I'm not sure if them were the best engines to be honest I haven't seen many 395's, but it moved right along, the tranny sucked but if you guys ever have a chance to look at one closely and play with it, them 59 Plymouth is a nice car, the seats turned to let you out of the car, the interior is a work of art.
I wish I never sold the car, back then I was kind of doing it to fund the other cars, and it seemed so ugly, now that I am older I appreciate it a lot and would love to own one for sunday breakfasts. Plus I got $9500 for it and now its probably worth $50-$75k
I had a point, maybe the motor is good just needs some love.