Wasn't able to listen to much of the speech unfortunaly but I do have a few thoughts about the Obama plan.
First and foremost, there basically is no good answer in Afghanistan. None.
Before I heard about the withdrawal time line my thought was that fulfilling McChrystal's request for troops was tactically a smart move (morally is another question). The general got what he wanted and if things don't improve no one can blame Obama for not listening to the general. I thought that it set Obama up nicely to pull the rip cord on the whole thing in the not-so distant future, "Hey, we tried it your way and it's not working. We're getting out."
The time line is an interesting curveball. From a military perspective I think that it improves our standing on the ground with ordinary Afghani's who are weary of decades long foreign occupation. We're leaving and not after pre-conditions are met, we've set a date and we're leaving. It also puts a hard and fast deadline on the Afghan government to get their act together, something that has long been needed in my opinion. As far as the Taliban goes it will be interesting to see if they ramp up attacks or if they lay in wait, biding their time for us to leave. If they lay in wait it may actually provide enough breathing room to give the government a fighting chance.
Domestically the time line probably tempers some of the outrage from Obama voters, it certainly did for me. I don't like the idea of adding more troops because I'm not convinced that it will make any appreciable difference - except in the American body count. At least though we can point to a firm date where we will be getting the hell out of there. I'm not happy but I think it's a decent compromise.
It's amazing the utter mess that BushCo. left behind. I really cannot imagine the pressure that the administration is under to fix Afghanistan, Iraq, the economy writ large, healthcare... Anyone of those things would be an incredible challenge.