I'm not sure that approaching contemporary anthropology is a whole is
the absolute best way to develop the knowledge that you
seek. Anthropologists study a bunch of different things, and while
knowing this stuff will help you be able to develop better designs and
products, this is a case where being a generalist is probably not an
effective use of time.
Anthropologists study culture, the superstructural stuff that
happens when you put a bunch of people in close proximity and let the
situation stew for a while. Apologies for the rough
definition. Knowing about culture, how cultures and societies
function, what causes them to break, what causes them to flourish is
fascinating and useful. Reading the "anthropological cannon" will help
you begin to understand this, but again long road, and I think the
questions you need answered are more easily addressed with some
specific projects.
First I'd like to just characterize Anthropology for a moment:
Although Anthropology isn't an experimental field, it's incredibly
empirical. Anthropologists collect a lot of data, and attempt to
describe what they see as totally as possible. This methodology, and
approach is--I think--extremely useful to software developers. It's
very easy to say "people want this," or "users feel this way," about a
feature or aspect of your software based on your experiences. It's
terribly difficult to figure out how users actually feel and interact
with your software in a precise way. If you had to take one
Anthropology class as a software developer, I'd recommend something
with a methodological emphasis.
In terms of specific resources, the following directions spring to mind
Dona Harroway's "The Cyborg Manifesto," springs instantly to mind as
the foundational work in a field of study that explores the
interaction between people, and machines as a social phenomena. It's
short. Good read. Amber Case, a young "cyborg anthropologist" does
work in Harroway's tradition, and I'd follow up on both of these
folks.
Secondly, I'd explore studies of cities and small communities. Except
in some very extreme cases (i.e. Twitter, Facebook, etc.), whole
cultures aren't using your software. Groups are. Learn about them. I
think urban studies and work that gets called "urban sociology" might
begin to provide you the kinds of answer that you'd be interested
in. I think that would be a good place to start.