no issue making a 440 run in the low 12s
I highly recommend using a good forged piston , the cost difference is only $200 & the gaskets would cost that
I can help you order a cam that will make the power you want
honestly I would spend the $$ on a 440 source stroker kit & build a 512 CI , it will cost about the same or less as rebuilding the old parts anyway
The radiator is iffy , how big is the rad now ?
you really need a triple core 22" minimum for a big block , 26 " better obviously