This thesis explores the details and profitability of two distinct operational strategies utilized by dairy operations as alternatives to expanding milk production. It features farms that have either transitioned to organic production or installed a farm-scale anaerobic digester, motivated in part by the opportunity for market specialization or income diversification to increase the viability of their dairy farm businesses. The first analysis examines the demographics and production characteristics impacting the profitability of organic dairy farmers in Vermont and Maine. This provides policymakers, educators, lenders, and suppliers with a profile of this sector that accounts for 23% of dairy farms in Vermont and 20% of dairy farms in Maine, annually shipping, on average, 787,600 lbs. milk per farm. The study was conducted through a longitudinal survey of 83 organic farmers in Vermont and Maine from 2004 to 2012. A multiple linear regression analysis of the sample demonstrated six significant variables that affect farm profitability measured by return on assets (ROA). Having at least 80% Holstein herd composition, increasing the daily pounds of grain fed to cows during the winter months, a primary farm operator having grown-up on dairy farm, and the use of feed mixing machinery all positively impacted ROA. Farm profitability was negatively affected on farms with a high rate of annual cow morbidity and also tended to decrease over the course of the survey as organic prices leveled. While the model developed here has some explanatory power (R2 = 0.387), variability in farm profitability is affected by complex economic pressures. The second analysis reports the predicted and actual annual maintenance figures collected from anaerobic digester systems in Vermont. Within Vermont, 16 farms operate methane-generating ADS. All of these farms have received some form of public funds and/or a voluntary consumer premium. The analysis compares costs by creating a ratio of actual maintenance, repair, oil, and labor costs over these same predicted costs. This ratio is used to assess whether the suggested industry operating cost estimator tends to over or under predict annual maintenance costs. The ratio was evaluated with a one-way Student's t-test (p = 0.046) finding that maintenance costs tend to be under-predicted compared to the actual costs. One-way ANOVA was used to determine a statistically significant effect of herd size (F = 6.453, p = 0.052), showing that the maintenance ratio varies significantly between groups, This analysis indicates that predicting annual maintenance, repairs, and labor costs as a function of 3.5% of total kWh production is an acceptable method for digesters on farms with more than 500 cows, but under predicts maintenance costs for smaller farms. For smaller farms, the actual costs were on average 2.5 times higher.