He absolutely is a hypocrite.
He acts like it wasn't a big deal, and has no plans to change the way we deal with drugs.
He could remove marijuana from schedule one if he wanted to, but has no plans to do so. That would make his bosses mad.
He said the feds would not go after dispensaries. The pharmaceutical people that gave him all those millions told him he can't say that. So he sent out another memo saying every one is subject to raids.
That is hypocritical.
His cavalier attitude about his own drug use is hypocritical. It is like saying it was fine, no big deal, but don't you do it, or you will be subject to arrest. He has the power, allegedly, to affect change. He has no plans to do so.
It is hypocritical and was an asshole move.
"I got away with it, ha ha."
He did not say he wouldn't go after dispensaries, what he said was he wouldn't go after dispensaries on the Federal Level as long as they were compliant with state laws. What that really means is that he wasn't going to change the laws but where possible he'd allow the states to decide who was breaking them.
Also the memo you refer to him was not sent out by him. The people that are responsible have come out publically on record that they acted on thier own accord with no prior approval or involvement from the White House. Unfortunately that doesn't fit your fantasy story that it's all Obama's fault. So you just make shit up to make things fit your fantasy. If Obama really wanted to go after dispensaries he would just do it, across the board, no warning, no giving a chance for them to just close shop and walk away. The fact of the matter is one of two things. Either the people behind the dispensaries untouched are in collusion with the government to take control of the market or the dispensaries that were targeted were not as compliant as everyone wants to believe. The claim of the US Attornies of California was that the dispensaries targeted were using the relaxed position of the Federal Government to move marijuana across state lines. This would be something that most if not all users of the dispensaries would be totally unaware of and it would make the dispensaries in question clearly non compliant.
Finally you have no way of knowing he had the attitude of "Haha I got away with it" that's you making up what he thought to support your position against him. It's far more likely that he thought something more like "Well, this shit is kind of fun and all but if I want to go to harvad and have a future in law and/or politics, I better stop messing with this stuff before I get busted." Him not doing anything to legalize it when given the theoretical opportunity is in no way hypocritical to his decision to not keep using marijuana. In fact legalizing it would be more hypocritical to what his thoughts on the matter were when he stopped using then not legalizing it is. You're just mad because you convinced yourself, based on typical political doublespeak (saying things that allows people to believe what they want to believe without really commiting yourself one way or another), that he was going to legalize marijuana.