Let's say I have an older system/framework that's showing its age a bit, but will soon be leveraged to do much more than it was first intended to do. It's a web app that didn't have a lot of common codebehind in it, so I've proposed that it will be less man-hour effort in the long run to rebuild it using more forward-looking code, with an eye for reducing maintenance effort (I've owned the legacy system for some time now and believe this to be true). Keep in mind the architecture of the legacy system does end up requiring a lot of troubleshooting and TLC: I don't care that it's not "pretty" or written "properly" if it works, but it doesn't "just work" as it is right now. I've done rewrites before successfully with a similar system, and it looks like the powers that be are open to me doing it, provided I propose it correctly.
So now it's up to me to sell the idea. The previous system I mentioned I successfully rewrote was nothing formal, sort of an in-my-spare-time, but this has immediate impact on project timelines if I spend some upfront time in the rewrite. This means I better know my stuff. Having not officially justified a complete rewrite before, I'd like ideas on how to pitch it.
Immediately I'll need to scope the rewrite, of course, but after that it's fuzzy. It'd help to have numbers proving the maintenance costs and savings after the rewrite, but that's tricky to estimate. Anything else?