Cool car! I helped a buddy swap a 5.3/4l60e into a '59 Brookwood 2 door wagon, and now am helping his son on another'59 2door Brookwood. The first one we cut the top out of a late 80's S10 gas tank and welded it in the original tank and used the S10 sender with a Walbro pump. Been on the road a couple of years and works good. His son had an aluminum tank fabbed at a hot rod shop and is using a Tanks sender and pump, but its not running yet.
You will at least need an F body oil pan, and will most likely need to clearance the front crossmember a bit, but not a whole lot.
Good luck with it and post some more pics when you get started.
Also, just curious, you do a lot of surfing in Kentucky?

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