"If you like your healthcare plan you can keep it, period". Why would you bother parsing what he said word by word. He lies, period. What he says means nothing.
Well in that case, there were some things that needed clarification. For one, the people without actual heatlhcare plans - the guys who payed their dealer in monthly installments weren't eligible to keep their plans. But the biggest issues was, the government doesn't actually control private enterprise, so they found a loophole where they could switch people off the plans they had before the cutoff (of the plans they could keep) to a brand new one with the same benefits. Then when the law came into effect the insurance companies said "oh darn, your cheap plan doesn't meet the minimum requirements, and it's too new so you can't keep it - Obama made us cancel it".
If Obama was a dictator, then he could say things about the future, but since corporations don't listen to the president, and Congress certainly isn't going to do exactly what he wants, it means the statements are what he hopes to happen - he doesn't have a crystal ball.
The president especially should be forward thinking in government - and we want him to share those thoughts with us. Since he's actually in charge of running a lot of the government, it might be a good idea to listen to him. Some speeches like this NSA one are full of weasel words, but since he's stating what the policy is going to be (at least officially), it's worth figuring out what he's saying.