Thull-
According to my OSO if you get through TBS with a stellar performance the waiver is pretty easy to get. Remember, the age used to be set at 30. They lowered it due to the high number of applicants at the time and some doctor at NAMI who said you stop retaining as much information as you get older. TBS flight slots are a case by case situation, not a group effort. If you can prove yourself and make a case for your package then you should be ok. In your case you need to ask yourself if you are doing this for the right reason. My professor posed this question to me. Do you love your country enough to say that even if you don't get the flight slot..... I am prepared to LEAD MARINES? Tough question and for this reason you should really think about the situation. Also, consider this. With your age, the longer you wait, the tougher it continues to get for you. (because you continue to get older) i.e. OCC 193, 194, 195 etc.... and eventually the reviewing board will start to question why you won't accept a contract to become a MARINE OFFICER. I only write so much because I've gone through the same exact situation you have and sympathize with it. Good luck to you in your decision.
Ric