The simplest solution, to me, is to just distribute containers (or some other sandbox) with wine in it, and the necessary shenanigans to get the windows program (just the one) working in the container, and just distribute that. Everyone gets the same artifact, and it always works. No more dicking around with wine settings, because it's baked in for whatever the software is.
Yes, this is tremendously space inefficient, so the next step would be a way of slimming wine down for container usage.
The only real barrier to this system is licensing and software anti patterns. You might have to do some dark magic to install the software in the container in the first place.