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Consistently broken (with each new release upstream, in other words, not "broken at all times") is kind of the norm in the Linux world. While MS goes to great lengths to keep Windows backwards compatible every which way, the various Linux projects regularly break APIs and backwards compatibility.

Part of this is that they don't want the baggage of having to support APIs and code that are no longer current, and people have said that Windows' insistence on backwards compatibility has held it back. Often the "best" way of doing things in one release is discovered not to be that great by the next one; Windows would tend to extend and issue workarounds to preserve the backwards compatibility, and "Linux", as we call it, would usually not bother, opting to tolerate the short-term pain of breakage rather than the long-term pain of having to maintain the legacy code forever.

Of course, Windows is a single product, where the world of Linux is many, many different and independent projects that are all "Linux" in people's minds. If each Linux project were to say, "We've got to break this API to move forward. We haven't broken anything in years, but now it's time," you'd have many, many breakages in the end product, even though each project only decided to break one thing in their respective products. There's no centralized leader to tell them NO, go back to the drawing board and figure out a way to do this without breaking the old code... and few people would really want there to be.

Windows, being under centralized control, could just as easily receive requests from every department leader from various parts of Windows to allow breakage so that they can move forward, but the Windows leader is not likely to approve dozens upon dozens of breakages, even if the department leaders each see their proposed breakage as being the only one. What looks like a once-in-a-blue-moon to a leader of a project that is a small bit of the whole can be a near constant when the scope is the entire thing (Windows or a complete distro as offered).

It does increase the work load on downstream teams if the upstream stuff keeps changing, but if you want to go in a different direction, it's a necessary evil if you want to benefit from the other work put into a given project upstream. It's not just Linux that has this issue... I think of Pale Moon and Firefox, where much of the work in Pale Moon is just stripping out the dumb stuff Firefox decided on months or years ago. The farther FF gets from its roots, the harder this will become.

PM is committed to maintaining powerful XUL addons, but FF is set to abandon them in less than a year as part of their never-ending quest to become Chrome. I really hope it works out, but I am concerned that the workload may become too much to handle. There are a bunch of addons I simply will not live without... Firefox (or its derivatives), properly extended, is the only usable browser in existence, IMO.

I don't know if Ubuntu has completely jettisoned Upstart, as it has been a while since I used Ubuntu proper, but their downstream derivative Mint still comes with your choice of Upstart or SystemD (simply select which you want in GRUB at boot time; both are installed by default). Since MATE and Cinnamon are based on GNOME, I would assume that they have to have their support for Upstart backported with each upstream Ubuntu release too, which is probably one of a few reasons Mint has taken to only using Ubuntu LTS releases as their base.

A lot of work in Mint is about de-stupidizing what has been done upstream... the X project (not to be confused with X servers) is one such thing, which aims to take the various g* programs (like ged) and stripping out the hamburger menus and other such detritus, and restoring them to a desktop-appropriate UI. Each time an upstream version of ged or whatever else changes, the Mint devs have to backport the change into their own version (or decide it's not worth it).

De-stupidizing UIs is big these days... reminds me of how much work I had to do after installing Windows 8.1 to make it into a reasonable desktop OS. Windows 10... can't reasonably be done there; I've written it off as a lost cause.