Data are presented from structured interviews conducted with 340 youths from the Monroe-Pratt neighborhood of Baltimore (Maryland). Interviews reveal lifestyle and community environmental factors that increase the risks of youth experiencing failure in educational and occupational attainment. Suggestions are made for improving the educational climate and educational practices. The interviews were conducted as part of the Young Adult AIDS Prevention Project. Sixty-one percent of the sample was White, with 35 percent African American, and nearly equal numbers of males and females. Factors considered included: (1) the home environment; (2) peer relationships; (3) community threats and resources; (4) alcohol and other drugs; (5) mental health problems; (6) dating and sexual behavior; (7) early parenthood; and (8) jobs and educational aspirations. Existing educational programs are reviewed, and suggestions are made for rethinking educational programs for multiproblem youth. Practical approaches are outlined to improve neighborhood training programs, reduce dropouts, and promote family communication and parent participation. An example is given of a proposed innovative, collaborative educational program for multiproblem youth. Ten tables illustrate the discussion and provide additional information about the survey sample. (Contains 32 references.) (SLD)