This work presents case studies of Structural Health Monitoring (SHM), both direct and indirect, implemented on bridges in Chile by LIND Engineering and its team. The objective of the study is to document and compare different instrumentation and/or non-destructive testing strategies applied to road and railway infrastructure, with the purpose of extracting best practices and generating guidelines for future SHM projects in Latin America. The applied methodology combines experiences of direct monitoring, through non-destructive testing, temporary instrumentation, and permanent systems installed on bridges of various typologies, together with an initial practical implementation of indirect monitoring, based on the instrumentation of forestry and railway vehicles to estimate the dynamic response of bridges during transit. Case studies include monitoring projects in mining infrastructure (2015–2017), the diagnosis of eight bridges in the O’Higgins Region (2021), the controlled unloading of a curved access bridge to an industrial plant during its construction phase (2023), the post-repair evaluation of a railway span (2023), as well as continuous monitoring efforts on the La Mochita Bridge (2020), Coihue Bridge (2021), Verde and La Raya Bridges, and four railway bridges between Maule and Biobío (2023–present). This presentation will focus on grouping the main objectives of the different approaches to testing and/or monitoring, highlighting key lessons learned, best practices, principal findings, and reported benefits, while also reflecting on the current state of the SHM market in order to encourage future projects. The results of direct monitoring confirm its capability to accurately characterize structural condition under critical scenarios and during construction processes, by identifying relevant physical variables for each instrumentation setup. On the other hand, indirect monitoring remains in a validation phase, with promising preliminary results suggesting potential benefits in terms of coverage and operational efficiency. In conclusion, the study demonstrates that integrating direct techniques with the progressive development of indirect methodologies enhances the management of structural health in critical infrastructures in Chile.