How would you begin improving on a really bad system?
Let me explain what I mean before you recommend creating unit tests and refactoring. I could use those techniques but that would be pointless in this case.
Actually the system is so broken it doesn't do what it needs to do.
For example the system should count how many messages it sends. It mostly works but in some cases it "forgets" to increase the value of the message counter. The problem is that so many other modules with their own workarounds build upon this counter that if I correct the counter the system as a whole would become worse than it is currently. The solution could be to modify all the modules and remove their own corrections, but with 150+ modules that would require so much coordination that I can not afford it.
Even worse, there are some problems that has workarounds not in the system itself, but in people's head. For example the system can not represent more than four related messages in one message group. Some services would require five messages grouped together. The accounting department knows about this limitation and every time they count the messages for these services, they count the message groups and multiply it by 5/4 to get the correct number of the messages. There is absolutely no documentation about these deviations and nobody knows how many such things are present in the system now.
So how would you begin working on improving this system? What strategy would you follow?
A few additional things: I'm a one-men-army working on this so it is not an acceptable answer to hire enough men and redesign/refactor the system. And in a few weeks or months I really should show some visible progression so it is not an option either to do the refactoring myself in a couple of years.
Some technical details: the system is written in Java and PHP but I don't think that really matters. There are two databases behind it, an Oracle and a PostgreSQL one. Besides the flaws mentioned before the code itself is smells too, it is really badly written and documented.
Additional info:
The counter issue is not a synchronization problem. The counter++ statements are added to some modules, and are not added to some other modules. A quick and dirty fix is to add them where they are missing. The long solution is to make it kind of an aspect for the modules that need it, making impossible to forget it later. I have no problems with fixing things like this, but if I would make this change I would break over 10 other modules.
Update:
I accepted Greg D's answer. Even if I like Adam Bellaire's more, it wouldn't help me to know what would be ideal to know. Thanks all for the answers.
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Lather, rinse, repeat! :)
Given time, consider adding unit tests for your new model one level underneath your interfaces with the rest of the system. Don't engrave the bad interfaces in code via tests that use them, you'll be changing them in a future iteration.
Addressing the particular issues you mention:
When you run into a situation that users are working around manually, talk with the users about changing it. Verify that they'll accept the change if you provide it before sinking the time into it. If they don't want the change, your job is to maintain the broken behavior.
When you run into a buggy component that multiple other components have worked around, I espouse a parallel component technique. Create a counter that works how the existing one should work. Provide a similar (or, if practical, identical) interface and slide the new component into the codebase. When you touch external components that work around the broken one, try to replace the old component with the new one. Similar interfaces ease porting of the code, and the old component is still around if the new one fails. Don't remove the old component until you can.
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