Some things to consider. You say you had the body off of the frame once before. Even though you had a shim under one radiator side, how did the hood fit before? What was the condition of the rubber pads under the front cowl mounts? I would really consider those questions before arbitrarily making new holes to relocate the radiator.
Someone told me this works, It is described as 30/31 but a shim might help. You could loosen the front cowl bolts and play with it. Playing with it sure beats modifications.
https://www.snydersantiqueauto.com/cowl-shim-set
I am eager to hear how it goes. I currently have my body up and off the frame as I am putting down new frame welting. I will be re-aligning soon enough too. Mine is also a '29 Tudor.