The Organizations have been investing more in Technology and Infrastructure spends like software upgrades, software renewals, software replacements, platform migrations etc., apart from investment in Business, People, and Processes. In this context, it is not an easy task for stakeholders to decide whether to go for a software upgrade or to replace it with another software. There is no unified approach or solution to consolidate data and relationships of Information Technology Assets, Software Upgrades, Software costs, Software defects, Software Performance Metrics, Security issues, IT system versions, service level objectives etc. Due to this, the decision making of software upgrades and software decommissioning is a tedious process and takes more time and effort. There is a need to build a solution that can integrate and validate the information like software assets, software upgrade success and failure likelihoods, cost benefit analysis of Cloud Computing, software metrics for fault prediction, software maintainability prediction results, Digital Transformation readiness and other related factors. There is an opportunity to apply Machine Learning techniques in defining and deriving the success likelihoods on the following data: Systems and data integration, software assets compatibility, operational service level agreement breaches, quality assurance metrics, security issues, number of open defects, number of defect fixes, number of priority incidents, mean time to resolve critical incidents, expected cost increase in software maintenance, potential cost reduction with the software or hardware replacement etc. This Research Proposal outlines the above mentioned to build a recommendation system aka decision tree namely Software Upgrades or Decommissions Life Cycle.