I'm known for being extremely harsh on applicants to our guild, even after I retired from being GM. I nitpick every single applicant that goes on our forum, point out their stupidity and most likely insult them a bit just for fun.
That said, if you wrote an application with the same tone of honesty and eloquence as you did in this post, I would get the vibe from you that you were a serious guy that would be worth considering and most likely let it slide through to the officers.
Don't try to conceal anything, tell them the full story and thereby paint a picture of what type of guy/girl you are, and let the "judges" vote on your merits as a person. In most cases, personality affects contribution to the roster, and all serious officers know that.