I disagree. I think it's more of a waiting game. The next generation, my generation, doesn't have stupid prejudices against words like "socialism." We're pretty progressive about things innately, possibly because we grew up with the internet and I can sit here and talk to people with universal healthcare and they're doing just fine, not dying under the effects of oppressive government. As you said, the collapse of the Soviet Union still lingers, and a lot of that is the baby boomer generation.
Personally I look at people like Obama as someone who's sticking his finger in the dike and kind of waiting to pass it on. Yeah he's not going full hog on progressivism, but it's better than going further right. He's holding things back. Some things, anyway. I think this is a long game, though. People now are still worried about silly words and need to be taught first and foremost that Democrats and left leaning policies aren't the end of the world. If we allow Obamacare, which is barely a progressive policy at all, but nonetheless is characterized that way, to get repealed, then people will keep their stupid fears.
Along with all that, whatever president comes next will very very likely be the head of a recovering economy. Economists have said it will pick up no matter who's in office, and that's probably pretty true. With a Romney presidency he'd get credit for all that, even for things Obama started to put into place. That's bad. That's the last thing we need is people putting more faith into the bullshit that Romney and the right are spewing right now.