Notes:
This passport covers the last three three years (1936-1938) of his time in Italy. It has a lot of travel stamps in it which I am going to try to sort out.
Cover:
After October 5, 1938, all male Jews had to had "Israel" as their middle name (and all women "Sarah"). Looks like Dad wrote this on himself. In addition, the large red J had to be added to all passports, so the August 5, 1939 date written on the top relates to when this was added to this passport.
Page 2:
It is hard to read the date, but I think it is April 4, 1936. From this (and all the later German endorsements), it would appear that everything had to go through the German Consulate in Milan before he moved to Rome. Thus he would have been 21 in this photograph.