To me, legacy code has cost. Great cost. Certainly, but it's the kind of cost that comes with having a lot of users, so it falls into the "nice problem to have

To me, legacy code has cost. Great cost. Certainly, but it's the kind of cost that comes with having a lot of users, so it falls into the "nice problem to have" basket. If you've got no users, you have a lot more freedom to throw things away. I understand where you're coming from, because I also do mostly-sole-maintenance on a large codebase with all the issues that come with a 20 year legacy. One strategy that can work in such a situation where you can't maintain perfect backwards-compatibility forever is to boil the frogs slowly - gradually deprecate and remove features over a longish time frame, because a single changed or missing feature is easier to adapt to for the userbase than a whole slew at once (many people probably don't even use the feature and won't notice).