It's not physically possible to do away with labels and generalizations. Fundamentally, unless you work out everything from first Quantum Mechanical principles, you are generalizing. Just calling something a "chair" denies or obscures that individual thing's unique characteristics. Worse yet, there is no single quality or property, concrete, abstract or emergent — not even the function of sitting — that is shared by all things we ordinarily and without practical ambiguity label as "chairs".
The situation is even more severe in a social and political sense. It would be nice, I suppose, if we could philosophically examine each and every individual position in complete detail and come to a decision about what to do. However, the real world doesn't work that; it's not even close. Just moving the labels and generalizations from collections to positions doesn't eliminate them. In just a social sense, to actually avoid labels and generalizations we would have to evaluate each case distinctly, and in terms only of absolute universals. Furthermore almost all social, political positions are justified on generalizations about human psychology. Without these generalizations, most actual cases have to be decided on nothing more than one's own arbitrary preferences.
We can't do without labels, but of course our reliance on labels has its own problems. DBB identifies a big one:
You hear someone is a 'conservative' and then think you know all of their positions on various issues.It's worth noting that DBB makes at best a generalization: not everyone draws an absolute conclusion about any position from a label. At worst it's an overstatement: I doubt very many people — much less a predominant majority — draw conclusions about all of someone's positions from his or her label.
Still, it's possible to carelessly or lazily draw conclusions about someone's positions from their label. On the one hand, given that DBB's positions are probably not accurately characterized, even in general, by any of these "macropolitical" labels, it's understandable and not particularly objectionable that he himself should avoid them. On the other hand, if a labels is generally accurate, that some people could carelessly and lazily misinterpret them is not a very good reason to avoid the label. Carelessness and laziness are unavoidable. You can't actually reason carelessly or lazily; "lazy reasoning" is an oxymoron; reasoning is precise and accurate by definition. Reasoning is inherently complicated and difficult, and we can't simply abandon every tool, physical or cognitive, that is susceptible to misuse by morons and slackers.
But DBB doesn't just argue against words that label bundles of political positions, he also objects (in his first post) to labels which are both descriptive and pejorative, such as "misogynist" or "racist". Yes, labels can be overused and misused but the fact that we can determine a label is misused argues for its value. To simply deny a label is to deny the underlying reality that the label applies to, unless you want to simply apply a different label. To flatly deny these sorts of labels does as much violence to our ability to accurately describe the real world as does arbitrarily overusing them without connection to their relation to objective reality.
(For a humorous example consider the continuous relabeling of feces and the appliances we excrete into; every euphemism becomes literal and is then discarded in favor of a new euphemism. "Crap", for instance, used to be a euphemism; it's now almost as explicit and scatological as "shit".)
The world is a complicated place, and our social and political interactions one of the most complicated things about the world. It would be nice if we could just take a few simple principles and apply them universally and without exception. But that's not going to happen; more precisely, the last time that happened, during the middle ages, we suffered a millennium of oppression, stagnation and unimaginable human misery. The world is complicated; we're just going to have to deal with those complications.