Re-applying per se is definitely not a red flag. We often accept people on the nth try. But if you're reapplying with substantially the same thing each time, you're effectively just testing our consistency. It would be a better bet to change more than wording.
Thanks for the response! I actually did some research and used this video as a model for my application! As far as the re-applying I actually meant re-submitting* (I.e. I have never applied to YC before with any company, however I have re-submitted my app for this session probably 5 or 6 times) I'm guessing the comment below addresses that particular question?
Does this also apply for an application that was submitted before the deadline? More specifically, is it fine to make an edit to the application after the deadline period?
Video quality can be at least this raw:
http://news.ycombinator.com/item?id=855057