How long does it take to upgrade a fundamental part of your system?
For example, say you are on Java 1.5, how long would it take to goto Java 1.6?
Specifically, are there special cases that you need to concern yourself with? Can you upgrade this but not that? If you change this will you have to change that?
How long will it take you to rollout this change? Is it a fairly automated process or will it take a lot of manual work?
How long will it take you to test the entire system (each environment) with the change?
Technical debt and resistance to change are the enemies of software projects. Use this case, whether real today or hypothetical for the future, to slim down your project and make it run faster.
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