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.