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.
I hope you don't mind being a bit curious about this, as a hobby driver.
At what level of motorsports are you working? It sounds like you both semi-regularly work with new teams. And are you working with them as a programmer? I'd be curious to know what kind of applications you're then working on, if so.
I work primarily with GT3 teams across the highest level championships (WEC, IMSA, DTM, GTWC, ALMS), with a variety of manufacturers.
With a small team of software engineers and data scientists, I'm building a cloud based motorsports data analysis platform which eliminates the friction involved in handling motorsports data and the differences between different manufacturers' software systems, and quickly gives drivers & coaches insights on how to improve their driving. So this involves getting into the weeds of a lot of this legacy software.
There are a few teams I work more closely with where I've set up their entire trackside network/tech stack, although nowadays I'm more focused on the software. Over the years I've done a bit of everything at the track, up to and including physically laying cables in a bare garage or setting up the systems on the car, although I don't do anything related to vehicle dynamics.
If the software is as ancient as you say, then surely you should be able to get away with installing an old copy of Win7 or even older? When you say "weird networking" do you imply internet as well? If it's all offline and only locally networked I see no reason why you need to run a modern version of windows.
I’ve tried emulators but performance is abysmal for these apps. There are also all sorts of weird networking things that don’t work.
And generally when you work with a new team which has a different tech stack, there just isn’t time within the context of a race weekend to faff.
I’m unfortunately locked in.