"There's a difference between talking to nazis or hardcore right wingers and talking to politically relatively inactive or unaware people who end up voting for republicans, and I think that distinction gets lost in a lot of the discourse."
In my post, I mostly talked about the silliness of trying to convince Nazis. DeBoer, in the post I critiqued, was talking more about trying to convince the sleeping masses—so, inactive or unaware people, who can be persuaded to vote Democrat, or embrace socialist revolution, or some such. Mea culpa for the strawmanning, and I'll try to explain briefly why this plan doesn't make sense either.
It's absolutely true that there are some number of people who don't pay much attention to politics and are therefore relatively loosely attached to one party or the other. If there's a massive recession, they may vote for Obama. Then they may drift back to the GOP. Surely, addressing these people respectfully and offering them programs that speak to them directly could get them on your side. Right?
Well, here's the problem. People who aren't paying attention to politics are by definition not paying attention to politics. Folks who are only loosely attached to one party or the other are generally loosely attached because they're not super engaged. Talking to them is difficult because people who aren't listening are, again by definition, not listening. Engaging folks who aren't engaged is very difficult, because you can't speak to them to tell them to pay attention unless they're paying attention.
Folks move back and forth between parties for reasons that are somewhat predictable, but frustrating for anyone who believes in the virtues of reasoned discourse. When the economy is crap, people vote against incumbents, even if the incumbents aren't to blame (see 2010.) And people tend to vote against the in party after a while no matter what. Getting a third term without incumbency is hard because people just get bored with the people in power, regardless of any other factor. You can read this as principled anti establishment fervor if you're determined, but it probably has as much to do with the out party being more motivated for change, the in party being complacent, and/or the fact that whoever's in power gets blamed for everything that goes wrong (people just take the stuff that goes right for granted.)
So, does that mean politics is hopeless? Not at all! There are things you can do to increase engagement—things like making it easier to vote and expanding the franchise, for example. Getting more people to vote engages more people in lots of ways. But that's not exactly convincing anybody of anything.
This also suggests that focusing on the least engaged people is not necessarily as clever as it sounds. There's a reason politicians are responsive to organized and motivated interest groups. Those groups vote, donate, organize, and pay attention. Some people paint any of these activist groups as elite and out of touch; Berkeley protestors don't understand the WWC, amiright? But this is dumb; of course any motivated person doesn't represent the bulk of unmotivated voters; again, this is definitional. The mistake is thinking that those unmotivated voters have strong political preferences. They don't; they're unmotivated!
Rather than pretending to speak for some phantom non-elite authentic voter who doesn't care about anti-fascist protest, why not engage with the motivated groups that motivate you—and work to amplify and legitimize folks who are doing things you think is worthwhile. Don't spit on the folks who are doing the work in the name of random folks somewhere else who appeal to you demographically but aren't actually tuned in. Show solidarity with the people who show up. Showing passion and winning victories is more likely to appeal to people on the fence, anyway, than endless whining about how the coalition you have isn't good enough.