I do this same thing every year. 30 days before this one expires you do the same thing all over again. They will stamp his passport saying it's under consideration. Then they will stamp it again with the extension. So two stamps every time. Also remember to greet a reentry permit if he plans to go out of country.
Sorry but how does someone prove they are retired. I retired from one employer and get a pension from them. So I guess I an retired. Even though I went to work for someone else a month later.