Over the past 15 years, major advances in Concentrating Photovoltaics (CPV) have been achieved. Ultra-efficient Si solar cells have produced commercial concentration systems which are being fielded today and are competitively priced. Advanced research has primarily focused on significantly more efficient multi-junction solar cells for tomorrow's systems. This effort has produced sophisticated solar cells that significantly improve power production. Additional performance and cost improvements, especially in the optical system area and system integration, must be made before CPV can realize its ultimate commercial potential. Structural integrity and reliability are vital for commercial success. As incremental technical improvements are made in solar cell technologies, evaluation and 'fine-tuning' of optical systems properly matched to the solar cell are becoming increasingly necessary. As we move forward, it is increasingly important to optimize all of the interrelated elements of a CPV system for high performance without sacrificing the marketable cost and structural requirements of the system. Areas such as wavelength absorption of refractive optics need to be carefully matched to the solar cell technology employed. Reflective optics require advanced engineering models to insure uniform flux distribution without excessive losses. In Situ measurement of the 'fine-grain' improvements are difficult as multiple variables such as solar insolation, temperature, wind, altitude, etc. infringe on analytical data. This paper discusses design considerations based on 10 years of field trials of high concentration systems and their relevance for tomorrow's advanced CPV systems.