An investigative study on community, reliability and usability of CFEngine, Chef and Puppet is represented in this paper. This research study attempts to quantify software qualities like community, reliability and usability of these products and analyses the result to figure out if any product stands out in any of these qualities. Comprehending software characteristics like community, usability and reliability is complex operation often making it challenging tomake a quantifiable measurement on them. Research is made in this paper to explore and make these qualities measurable and quantifiable through the application of different statistical and mathematical model. Product popularity trend, resources available for product, community structure as well as it s field support is studied utilizing different sources like Google, Hackers news andusers mailing list. Reliability growth in latest three version of these product is examined by application of Weibull distribution on data obtained from individual bug repository. Finally the usability test is conducted to cover both subjective and objective aspect of user experience on these product to measure each product s usability and study the difference in usability offered by each. This research hopes to pave the way for future research into this area and helppeople to comprehend community ,reliability and usability of these products.