Forest-related practitioner’s harvest/business expansion decisions are important in that these decisions, although individually made, have a cumulative influence on the overall prosperity of the forest products industry and forest coverage in Massachusetts. This paper explored the decision making process of five stakeholder groups in Massachusetts’ forest products production and distribution chain - landowners, foresters, loggers, sawmills, and wholesalers - aiming to find out what factors or specific possible reasons influence each stakeholder’s harvest/business expansion decisions. In recent years, Massachusetts has had a shrinking forest products industry despite a healthy forest with growing tree volumes. This has led to a dependence on imports for its local forest products consumption. To solve this problem, Damery, Yadav, & Zhao (2008) surveyed landowners, foresters, loggers, sawmills and wholesalers to identify barriers to expansion of the local forest products industry. This paper takes advantage of the data gathered and conducts further analysis to answer the question: despite the barriers, why do some practitioners still choose to make harvest/business expansion decisions while others do not? For landowners, foresters, and loggers who have sufficient useful responses, quantitative analysis was conducted through statistical hypothesis testing and econometric modeling to identify causal factors that may lead to the differences. Factors of significance were: 1) years of forestland ownership, 2) Chapter 61 enrollment, and 3) willingness to harvest with neighbors for landowners; 1) practicing years, 2) previous assisted harvest volumes, 3) workmen’s compensation concern, and 4) small-diameter log markets emphasis for foresters; and 1) nature of logging operation (hobby/part-time/full-time), and 2) competition concern for loggers. Due to the small sample size for sawmills and wholesalers, qualitative analysis was conducted through anecdotal analysis to reveal specific possible reasons, rather than generalizable factors, that may explain different choices. Among all nine factors identified, five of them concerning stakeholder’s attitudes and choices have the potential to be influenced by policy. Programs that can: increase landowner enrollment in Chapter 61, promote cooperation with neighboring landowners, mitigate forester concern with workmen’s compensation, improve markets for small-diameter logs, or improve the competitive landscape for loggers, have the potential to increase production of Massachusetts native woods.