Having once worked with maintaining an ancient 3rd party windows desktop app, I'm surprised you don't have problems with them on recent windows. I guarantee you the developers do. They must be truly heroic maintainers if none of those frustrations bleed through to you.
A time will come when the easiest way to run these beasts is in a docker container running wine, and I don't think it will be long.
Plenty of frustrations pass along to me, but I am sure that the developers maintaining the software are also putting in a massive shift to make it all keep working. These companies are often quite small, or small underfunded teams within larger organisations, and I believe that they are doing a fantastic job working with what they have.
New features are few and far between, but that doesn't mean that they're not doing a good job. The current state of the industry is not a reflection of the developers working on it today, it's a decades long legacy.
A time will come when the easiest way to run these beasts is in a docker container running wine, and I don't think it will be long.