The technology startup landscape of South Kerala has grown substantially over the past decade, yet a systematic empirical understanding of the structural barriers that constrain startup development remains limited. This study investigates the multidimensional challenges faced by technology startups in Southern Kerala through a rigorously designed factor-analytic framework. Primary data were gathered from 300 founders and senior decision-makers of technology startups via a structured questionnaire encompassing 88 items spanning financial, operational, technological, market, human resource, and socio-environmental domains. Exploratory Factor Analysis (EFA) using Principal Component Analysis (PCA) with Varimax rotation was applied to identify the latent dimensions underlying the observed challenge variables. The Kaiser-Meyer-Olkin (KMO) measure of sampling adequacy registered 0.650, and Bartlett's Test of Sphericity was highly significant (χ² = 40015.063, df = 3828, p < 0.001), validating the factorability of the data. Eight factors were extracted, collectively accounting for 62.534% of the total variance: (1) Foundational Startup Challenges, (2) Operational Challenges, (3) Financial Constraints, (4) Market-Related Challenges, (5) Human Resource Management, (6) Organizational Processes, (7) Technological Barriers, and (8) Socio-Environmental Challenges. Financial and market-related factors emerged as the most pervasive constraints, while technological and organizational dimensions signal an emerging shift toward scalability concerns. The findings carry significant implications for policymakers, startup incubators, venture capital networks, and academic researchers seeking to strengthen the South Kerala startup ecosystem.