If you haven't worked with legacy systems, you may want to check out "Working Effectively With Legacy Code" http://www.amazon.com/gp/product/0131177052/ref=as_

If you haven't worked with legacy systems, you may want to check out "Working Effectively With Legacy Code" http://www.amazon.com/gp/product/0131177052/ref=as_li_ss_tl?ie=UTF8&tag=keysofgeni-20 http://www.amazon.com/gp/product/0131177052/ref=as_li_ss_tl?... You'll want to make your boss's profitable projects your top priority. Then gradually go through and start fixing the legacy problems bit by bit. Don't rewrite the entire system in a year, start rewriting/refactoring/fixing individual pieces of it one piece at a time. I had a municipal tax management application that was a complete mess full of spaghetti VB code, multiple instances of similar queries/calculations/interfaces sprinkled all across the app in different places with different implementations. I even had one screen with a 40,000 line event handler. Over the course of 2 years, the entire thing was whipped into shape, additional functionality was added, and now it's easy for the new maintainers to work with it.