I have no idea what the freelance box is unless they have updated again.
See how you get on further into the application. Just a little tip though, you MUST upload the documents they ask for, even if you think they don't apply. Without doing it, you will be stuck on the page and cannot move on or submit the application.
Tony probably not. After the recent update, further on in the application it starts to ask for all sorts of information. If it wants multiple flights during the visa life and at the end if it, I really don't know. You do realise your going to need a letter from his employer addressed specially to the Embassy? Also his bank statements/ pension income details.
Online where? If that is the London online embassy application site, it's because he's applying for the wrong visa. That's because you told the system he wants to stay 6 months. It's now trying to issue an O-A visa. You should be applying for a METV visa. That gives increments of 60 days after which you apply for a 30 day extension taking you to 90 days, then leave and reenter or leave after 60 days and come back in for another 60 days. He cannot stay for 6 months continually on that visa