1. One common complaint against Heidegger is that he is nostalgic. It seems that his sense of dwelling is rooted in an agrarian society, small communities, and in a pre-industrial or technologically limited age. While this might not be entirely fair, his examples always seem to reflect this, objections on his part notwithstanding. So, is the only way we can dwell, to get out of modern society?
2. Heidegger's sense of dwelling seems to be quite static. To dwell means to take root in a place. But don't some people dwell in other ways? Bedouins dwell by moving, for instance. They do not build cities, but move about a range, taking their tents and animals with them. They don't stay still, nor do they seem to build. Do they dwell?
3. Heidegger is known to have ascribed to at least some of the values of the Nazi movement during WWII, and possibly after as well. So what? Well, part of the mythology of National Socialism in Germany was Blut und Boden, blood and soil. The soil had an almost mystical attraction, and dwelling on that soil meant more than just living in a particular place. To what extent could we see those mystical values expressed here?
Now, one might still say, so what? The Nazis valued technological advancement too; for someone else to hold that value doesn't mean that they too are Nazis, or in any way sympathetic to them. We could still ask, though, whether Heidegger's sense of dwelling also has a sense of entitlement to it, that is, a sense that those who truly dwell in a place have a right to that place. That's the logic the Nazis used to extend their empire - they were just retaking the traditional land of the Germans.
So, Heidegger's specific analysis might not be perfect. But he has raised a significant question, which is, What is the relationship between ourselves and our places, particularly our built places? How do our places show us for what we are, and how do we show them for what they are?
And he does raise the other question, even in his limitations - if we think he's wrong, what do we think it means to dwell? What has he left out?