Jeremy, I just did an internet search to see if I could find some research studies on the subject and I still don't get it. What I mostly found were forum discussions, which I usually dismiss as opinion based on subjectivity.
Actual articles on the subject were fairly elusive, and for the most part made reference to Hip-Hop culture which they defined generally as an urban youth culture associated with rap music and the fashions of African-American residents of the inner city.
One by Dan Hodge, a youth minister in California, 'Wankstas & Wiggas: Dealing with the New Generation of White Hip Hop Culture' in part said, "What was once thought of as only a Black culture, hip hop has become a multi-ethnic, multi-dimensional culture that embodies a host of languages, colors, music, and life? Hip-hop culture is more than just the music itself; its a way of life for many." (http://www.cyfm.net/article.php?article=Wankstas_Wiggas.html)
(For those, like me, who are clueless regarding urban slang, a 'wanksta' is a person who acts/looks like a gangster or thug, but has never done anything gangster or thug-like besides acting or looking like one. A 'wigga' or 'wigger' is a white person who so admires black culture, lifestyle and fashions, that they adopt aspects of it for themselves, especially hip-hop culture. Now we know.)
I did find a reference to a book on the subject, "WHY WHITE KIDS LOVE HIP-HOP: Wankstas, Wiggers, Wannabes and the New Reality of Race in America" by Bakiri Kitswana. The book's blurb says, "The author looks at the culture of hip-hop and how race is being lived by young people. At the same time he addresses uncomfortable truths about America's level of comfort with black people and challenges preconceived notions of race such as whether culture belongs to a race in the first place." (http://facweb.eths.k12.il.us/booksrus/bookstoread.htm)
Part of a review I saw on it by a Rebecca Onion, went something like this: "Unfortunately, Bakari Kitwana's book, for which I had high hopes, doesn't address the psychological ramifications of the white-kid hip-hop explosion, tending instead towards vast generalizations about the shifting state of race politics in America." So, no deep answers there. No matter, I wasn't going to buy it anyway.
While scanning thru what I could find, I did see some references made to social issues like in-groups, popularity and even racialized masculinity. One twelve year old said, "At my school there's quite a lot of white boys trying to act black. They use the language that associate with 'gangsters' because they think it's cool. They wear their trousers down on their hips because they think it's "in". I think they act like this because they want to be accepted by boys acting like gangsters." Another said, "White kids nowadays try to act "black" - which means gangster. They act as if the words are interchangeable."
What I didn't see were any references or correlations made to the impact of greater social changes and what role this might play developmentally as today's kids attempt to find their own identity, struggle with social interactions, and grapple with moral issues. The world is surely a bigger, faster, more complex and scarier place than when I was young and I recall being plenty frightened and unsure of myself. If donning the mental cloak of a gangster makes them feel braver, stronger, and more sure of themselves, I'd say right there's part of the appeal. But maybe I go too deep.
All in all, my search turned up nothing conclusive other than the commonality of hip-hop. According to one reference, the term is most commonly used today as a synonym for rap music And I have only one opinion of rap music.