Scrap old code early and often. When in doubt, throw it out. The hard part is convincing non-technical folks of the cost-to-maintain.
So long as the value derived appears to be greater than the cost to operate and maintain, there's still positive value flowing from the software. The question surrounding a rewrite this: "will we get even more value from a rewrite?" Or alternatively "How much more value will we get from a rewrite?" How many person-hours of maintenance will you save?
Remember, the rewrite investment is once only. The return on the rewrite investment lasts forever. Forever.
Focus the value question down to specific issues. You listed a bunch of them above. Stick with that.
"Will we get more value by reducing cost through
dropping the junk that we don't use
but still have to wade through?"
"Will we get more value from dropping the junk that's unreliable and breaks?"
"Will we get more value if we understand it -- not by documenting, but by replacing with something we built as a team?"
Do you homework. You'll have to confront the following show-stoppers.
These will originate somewhere in your executive foodchain from someone who'll respond as follows:
"Is it broken?" And when you say "It's not crashed as such," They'll say "It's not broke - don't fix it."
"You've done the code analysis, you understand it, you no longer need to fix it."
What's your answer to them?
That's only the first hurdle. Here's the worst possible situation. This doesn't always happen, but it does happen with alarming frequency.
Someone in your executive foodchain will have this thought:
- "A rewrite doesn't create enough value. Rather than simply rewrite, let's expand it." The justification is that by creating enough value, users are more likely to buy in to the rewrite.
A project where scope is expanded -- artificially -- to add value is usually doomed.
Instead, do the smallest rewrite you can to replace the darn thing. Then expand to fit real needs and add value.