Quite a bit of replies with various good suggestions in a short span of time. However, I could not understand what exactly is the problem you are trying to solv

Quite a bit of replies with various good suggestions in a short span of time. However, I could not understand what exactly is the problem you are trying to solve? A $20m/year is pretty impressive with that kind of spaghetti code/tech amalgamation. It would be certainly a fun project for your more junior developers to dig into it and understand the actively used features. That raises my next question: what exactly is wrong with your 3-people development team? Are you expecting only 3 of them to make major changes, let alone a full rewrite for such a project? The way I see it is that you only have enough development resources to make minor changes or features that fit in the project's current spaghetti framework. Is that what management wants? If they want some big new features your only option is to find path of least resistance to implement them, especially if your budget is tight. Basically, add more hack-fixes and continue feeding the monstrous legacy. Unless you get more people, more budget you don't really have a choice of doing things "the proper way".