I've been out of status for more than 5 months right now, and I've been asked by my DSO to leave the USA and re enter sometime later. She couldn't give me a final answer about my visa status is it cancelled or not. I am voluntarily leaving the country within the next week. I just want to know how hard will it be for me to obtain a new F1 Visa. My visa is valid till 2016 and my I/94 got D/S written on it.
D/S means duration of status so as soon as your program was over your status expires and you have 60 days to leave (grace period). That the visa is valid until 2016 is not relevant in this case. You have not accrued unlawful presence until a judge has made such determination. I don't know what you mean by "cancel." You should take your DSO's advice. By remaining in the U.S. you are not changing anything.
Criminal Defense Attorney
You should consult an experience immigration attorney prior to your departure.