Dad had a 53 Super 88 Tudor when I was about 13 that I really liked. Great cars for rolling down the boulevard.
I'm doing a front disc brake conversion on my 51 Buick Special currently and getting close to completion hopefully. My booster will be located under the driver seat and required me to fab a bracket. The body style is the same to your ride so if you need ideas on booster location let me know. I am located not too far from you in Skokie. Love the car!