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Long term evolutionary needs for a system to be able to meet new and emerging requirements are often left unnoticed, since the complete picture is not apparently visible at the time of analysis. Therefore,over a long period of time, many of these systems become obsolete, because their lifecycles cannot be extended or are very expensive to re-engineer into are reusable system that could actually meet the new requirements. To overcome such difficulties, we present a methodology to build a wrapper-system based on the iterative object-process modeling scheme. The purpose of the wrapper-system is to coordinate three stages of iteration: first, to collect the evolving factors from the system behavior;second, to update system state, and third, to apply necessary changes to the system to meet new requirements. Based on our analyses of the system usage activity logs and detailed update-request history of several projects over two to three years of time, we show that this iterative scheme can be effectively applied for architecting evolvable systems with longer life expectancy.