After several years in which only superficial outcomes measures were used to evaluate grants funded by the Illinois Board of Higher Education (IBHE), the Illinois State University Center for the Study of Education Policy piloted a new approach by which real project assessment could be embedded in Improving Teacher Quality (ITQ) project designs when first funded in 2004. This approach applied logic modeling at both program and project levels. As a result, feedback about the program and the individual projects was integrated into evaluation at both of these programmatic levels. This article describes the details involved in seven years' work with the more sophisticated evaluation model. The ITQ program has moved from funding 26 Science, Technology, Engineering, and Mathematics projects with marginal evaluation plans to funding nine projects with solid, research-based logic models and aligned evaluation plans. The article also describes the difficulties involved in any attempt to compare one unique program with another, and instead uses the metaphor of the "investment portfolio" to both describe and assess the IBHE's array of investments in the ITQ projects. (Contains 4 figures and 1 table.)