As a point of interest, the engine in Norm Grabowskis T bucket was reportedly from his Dad's '52 Caddy. He somehow convinced his Pop that the engine was in need of a replacement, and he ended up with the old motor.

These Caddys were real powerhouses in their day. Guys like Bill Frick pioneered the Fordillac cars, where he swapped various Caddys into early '50's Fords. They made real screamers of those Fords. In the '50's the two engines most often swapped were the Caddy and Olds engines. Chryslers were popular, but large, and Buicks were just starting to appear, and the sbc didn't come out until '55.

300 hp is possible, but it will take some doing and some money. Most of it will be spent inside the engine doing stuff like balancing, boring, higher compression pistons, a good cam, and some SERIOUS head work. As Richard mentioned, parts availability will be not as good as more popular engines, however, I bought a lot of stuff from Egge Machine when I built the 394 in my Dodge truck. I think Mondello is also a source and can probably tell you how feasible it is to attempt this.

I wouldn't be too hung up on what hp you end up with, I would just do the normal hot rod tricks to the point your wallet starts to scream, and see how you like the way it runs. If you still want more go, break out another credit card.

Don