Those issues seem othorgonal to stable ABI issue from OP, specially the OpenGL one (that is more like a hardware incompatibility issue). When apps fail to run due to Wine updates, they are considered bugs to be fixed. On the native side, apps may break becuase: 1) required library is unavailable, normally because it is too old and unsupported; 2) required library's path is different in distro A from B. None of these are considered bugs and, as such, are rarely addressed. I believe Steam Linux Runtime is an attempt at fixing this,but I'm not sure about its effectiveness. Also, you are exaggerating on the "exact Wine version". It helps to know which versions don't have a regression by knowing which specific version an app used to run on.

In practice, Wine is constantly improving. It's in active development and not that stable, but regressions are mostly local. Treat its releases like bleeding edge.

>What works fine today will completely fail next year.

Usually not on the timescale of a year. I have many new games that worked a year ago and none of these stopped working now. The worst breakage I had recently was some physics glitches in an old RPG (released in 2001) on Wine 11.0, and it was fixed in the next release.