Oh, my dear old 500e, go and boil your head, you silly person... I entered flying a decade earlier than heliwanab did on the old life calendar and I was referred to as being a bit "advanced" in age at that time (I paid for my training with my youth and my government footed the financial bit, AFTER they had run me through the medical mangle). I am now a decade older than he and still doing the job for a living, so it certainly CAN be done.
But... if one can't pass the medical (and our candidate apparently has some concerns on that score), it's just plain silly to shell out all the training money up front, especially at 37ish if the good poultice-walloper tells you haven't a prayer of ever earning it back.
It would be the height of dunderheadedness to fail to get a full Class 1 before signing a training contract, and it would be the height of irresponsibility to recommend to him otherwise.