one huge issue with a lot of technical and product debt is that any re-write gets saddled with a huge dam of expectation bursting. Many people who have been told they can't have their feature for years because the volition of the software team has been close to zero (hence the rewrite) for so long suddenly push their demands onto the new product. Its hard for a re-write to focus on an MVP as a consequence.
Arguably it can be better to float a completely different boat and see if it swims but that can result in a product positioning problem where you then have two versions of the same product but with an uneven feature set.
Arguably it can be better to float a completely different boat and see if it swims but that can result in a product positioning problem where you then have two versions of the same product but with an uneven feature set.