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I would spend 5K for a decent paint job. Good from far, far from good so to speak and concentrate my funds on the drive train. The car can look great but if it don't go, its just a pretty garage ornament. A good "everything made in the USA" small block can run around ten grand. I know because I am currently having a 383 built for mine because like you, I want horsepower and the stock 302 in my car (also not the original motor)don't have it with todays crappy fuel and such. Be careful with crate engines. There are two cars in the shop where I am having my engine built that had failed summit crate engines in them. According to my mechanic, they used a lot of chinese parts in them. As old as these cars are, like someone said earlier, surprises like rot can and will pop up once you start stripping paint so that could throw a monkey wrench into your paint budget. If your car is a real SS396 I would put a big block back into it even though you don't have the original motor. If its not then I would build a stout small block for it. I am not nearly as knowledgeable as the other guys posting here. Im just relaying what I've learned through my recent experiences with my car. Ive spent a ton of money on my car but I love it and don't plan on selling it ever. So being "upside down" doesn't really concern me. Thats our hobby. Good luck with whatever you decide to do. You have a sweet car there!
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