Background: Homelessness is an increasing problem in Western European countries. Dutch local authorities initiated cross-sectional reviews to obtain accurate health and needs information on Homeless Service (HS) users. Methods: The Homeless People Treatment and Recovery (HOP-TR) study uses a comprehensive assessment strategy to obtain health data. Using a naturalistic meta-snowball sampling in 2015–2017, 436 Dutch HS users were assessed. The lived experience of HS users was the primary data source and was enriched with professional assessments. The InterRAI Community Mental Health questionnaire and “Homelessness Supplement” provided information in different areas of life. The approach for mental health assessments was transdiagnostic. Raw interview data were recoded to assess health and needs. The positive health framework structured symptomatic, social, and personal health domains relevant to recovery. Results: Most subjects were males, low educated, with a migration background. The majority were long-term or intermittently homeless. Concurrent health problems were present in two domains or more in most (95.0%) subjects. Almost all participants showed mental health problems (98.6%); for a significant share severe (72.5%). Frequent comorbid conditions were addiction (78%), chronic physical conditions (59.2%), and intellectual impairments (39.9%). Conclusion: The HOP-TR study reveals significant concurrent health problems among Dutch HS users. The interdependent character of different needs requires an integrated 3-D public health approach to comprehensively serve symptomatic, social, and personal dimensions, required to facilitate recovery.