With all of the expense and effort required to put a Y block into a vehicle that had a flat head, why not step up to the plate and install a later model 302 engine and trans into the car.
I had two small T-Birds for several years, a '56 & 57. Still have the '56 that has a 68 302 and a C-4 trans. The '57 was dead stock 312 w/AT. The 302 was much peppier than 312