The answer to your first question is no you don't have to but just make sure that the hole is covered by the fitting and no water ingress will get into the cavity.
If you run a cable in the cavity you are supposed to make allowances to the cable size as a cable in a cavity wall has to be slightly bigger in capacity due to external influences of the cavity wall insulation keeping the cable warm....
the house is early 70's construction and the is no insulation in the cavity. It looks like a 3" air gap between the inner and outer walls. I was going to use 1.5mm T&E or do you tink flex is better.