My final answer
It never ceases to amaze me how much guys are willing to help people through the forums on this website - thank you guys so much for all your inputs.
As tomorrow is my my last day to 7 day opt I think I will choose a separation date of 1 Aug 09 (original ADSC 7 Jun 09). With almost 90 days of leave stored up and only able to sell back 60 I will still get a full month off and get to sell back 60 days of 0-4 leave. This will put me available 1 July 09 and if by some crazy chance I get called for an earlier date I will beg and plead with my Sq/CC to let me take all of my leave making me available 1 May. You never know the AF might make me get out on my 7 Jun 09 ADSC date and all of this will not matter. Either way I am looking forward to something new and the next part of my life no matter how crazy things are.