I need a medical and a criminal waiver to join the army. If this is even possible how difficult will it be?

ok. I am 22 years old. about 3 years ago I was arrested because a stupid friend of mine robbed a gas station while I was driving (I had no idea he was doing this), anyway, he and I were arrested for (armed with a b.b. gun) robbery. In court it started as a class A felony but mine got moved down to just a class C felony "stealing" charge. I was put on probation with an SIS for 5 years. I screwed up and got a DWI on probation. Thats not all. last may I moved out of my parents house and lived with a friend of mine, to make the rest of this short I was arrested again when the police came to the house on a "public disturbance" call, and they smelled marijuana. Subsequently, they found a bag of pills in my (and my roomates) room. Nothing that they found belonged to me but the police did not know that there were two people living in that room, they only saw some utility bills in my name, so assumed it was my room. To clarify: I was home when this happened, my roomate was at work and so was not charged with anything. The next day my roomate came with me to my lawyers office and signed an affidavit stating that all of the things (pills, papers, marijuana grinder) in that room were his. ok to the point. I have a pending case which I am hoping I will not get any convictions for. I am on probation again for 5 years because of this arrest and DWI, my SIS was revoked and now have a permanent felony. I also was diagnosed with ADD when I was about 15, and have been prescribed adderall for it, but I honestly think that I was just a very lazy teenager, also, since all of this court and criminal business started I had some anxiety but firmly believe it is purely situational. I am prescribed clonazepam for that. I have been told by many people that it is still possible for me to get a waiver, and that they have friends and family with felonies that got waivers. I have also been told that it is possible to set an appointment with the judge presiding over my cases and ask him if he would expunge my probation if I could somehow show proof of enlistment eligibility and recieve a waiver for above conditions. I have done some reading on military websites about the importance of letters from doctors, family, employers and so on about me as a person and whether they think I am morally and medically able to complete training and be successfull in the military. I have read that the army recruiters do not just look at your offenses or medical problems and turn you away immediatly, rather, they (are supposed to) look at you as a whole person, not just a number that meets the requirements of enlistment. My brother is currently serving in the army and is deployed to afghanistan, my father was also in the Army and served during vietnam.

I know this is long question/explantion but regardless of my past I do not believe myself to be a "criminal" or "bad person" and hope that a recruiter and his higher-ups could see it that way too. I also scored a 90 on the pre-asvab.

PLEASE do not respond to this if you have nothing constructive to tell me. Regardless of your answers I will try as hard as I can to enlist. I am looking for some advice. your help is much appreciated.