If I'm brutally honest I think that having to apply is sort of a dumb practice. Now I'm probably one of the least known people in the town simply because I too am less than a month old on the server, but seriously, what does this application accomplish?
Anyone can answer these questions to your liking and still steal/destroy from the town. As you should know, people like to lie on the internet. Like I, I_Love_Miners has a dark/weird sense of humour. Clearly you didn't think it was funny, or know who Booker T is.
I'll take some of the blame on his "poor" application because I literally told him "they accept anyone, as long as you don't give the response 'Or else I'll give your mom cancer' to the question 'Why would you want to join Braavos?' you'll be ok.
That facts are, this guy likes to mine (can ya dig it?) and wants protection. He's new to minecraft and needs help. If he actually needs to re-apply and send a new application in, then I think I'll pack my bags as well, since I find the practice mind-boggling and unnecessary. That's my 2 cents.