My being "benevolent dictator until retirement" for the installer was probably not great for the community. But what you're mainly running into is an integration and testing problem. The UI needs to be tested on about five platforms, not just one, so we never developed a continuous testing and integration scheme that could protect against pull requests that broke things.
(By the way, it's actually much worse than five platforms if you count having to work with both custom built and platform versions of Python. And the testing load doubled with the need to work with both 2.7.x and 3.x. All this meant that a simple #.#.# update might require a couple of days of testing on three different machines [Linux, Windows, Mac] and multiple virtual environments [to cover recent versions of Red Hat and Debian flavors].)