[3] Prior to "white flight" in the 1960s and early 1970s, many neighborhoods in Southeast San Diego were subject to discriminatory restrictive covenants, a problem faced by African-Americans like former Councilman and Deputy Mayor George Stevens, who was denied the opportunity to purchase a house in the Skyline Hills from a white realtor.

With the great influx of Filipino immigrants joining the United States Navy,[5] especially from the Vietnam War era on to the 1990s, many Filipinos inhabited the Southeast San Diego neighborhoods of Alta Vista, Bay Terraces, Paradise Hills, Shelltown, Skyline Hills, and Valencia Park, both for the relatively affordable housing prices and its close proximity to Naval Base San Diego.

Much like the surrounding neighborhoods of Bay Terraces, Paradise Hills, and Jamacha-Lomita, Skyline is composed predominantly of low-density single-family homes spread across the hilly area.

[9] Much like other neighborhoods in Southeast San Diego, Skyline consists of postwar tract homes built in the 1950s and 1960's that have been outfitted with iron bars over the ground-floor windows and doors, as well as cast-iron gates and chain-link fences guarding driveways, a reflection of the perceived need for security in these historically high-crime urban neighborhoods.

[13] They have held a long-bitter rivalry with the Lincoln Park Bloods, which has been attributed to much of the violent crime and homicides across Southeast San Diego.

[14] Notable Hip Hop artist, Lecrae, who spent significant portions of his life living with his grandmother in Skyline, experienced much of the violence occurring in the community, and has paid tribute to the neighborhood in his songs including his 2013 single, "I'm Turnt," ("It's Southeast Daygo in the building, shout out to Peter Pan, Skyline, Imperial"),[15] and the 2019 single, "California Dreamin'" with 116, ("What up Southeast?