I really only know about volunteers and it's convoluted with social department into the mix also, but if you have a work permit, a letter from social, you get a one year visa. I can't see why flying to get a new visa is simpler/cheaper than immigration. The lawyer has to prepare documents either way and new visas have got to impact work permit applications.
It's onscreen at every border. Just because you use fake addresses on every form you fill in and think you are funny. You may be detained at said border and not allowed back. That would be fun wouldn't it?
It's a Monday! Don't stress. They will get everyone processed. If you don't want to wait go on a Friday and pickup Monday afternoon. 5 minutes tops to do both, but you have to spend a weekend in hell.
Why did he get a tourist visa? Why didn't he get the appropriate O-A retirement visa, which allows you an easier process to the retirement visa extension.