If my employers admins had to do all that in addition to what they already do (mostly make work for themselves to justify their pay) we would have to double the IT admin department so the answer from my employer would be NO!
Doesn't that mean that your entire argument boils down to
"you need to make it cheaper for me!"Microsofts desktop near-monopoly for two decades means that most admins and desktop software developers have a Microsoft mindset. (There is nothing sinister about that, it happens in every industry where there is one tool/device brand that has a clear majority.)
It is harder for those people to learn any other mindset, because they first have to unlearn things; and people who consider themselves "professionals" have a lot invested in their current mindset, and are naturally reluctant to go back to basics. It is much easier to leave them be, and just teach completely new people. (You can disagree if you like, but I have seen this in practice; it is a commonly observed fact, and not limited to IT tools.) We can see this for example in how processor manufacturers are shifting away from providing their own compilers, and instead increasingly support GCC (and hopefully LLVM, although I am less certain of that); the high-cost "enterprise" stuff remains, but is stagnant compared to the open source development.
When organizations consider moving from e.g. Windows to Linux desktops, the counterpressure is from people who do not want to unlearn old ways and learn new tools. From their perspective, it is a waste of their efforts, as they can already do the job. Because of Android phones, typical office desktop users adapt rather quickly, but the support staff faces huge problems. In fact, in many cases it would be more cost effective to just replace the entire support staff (up to and including the CTO), but for various reasons, that is usually not feasible.
A practical intermediate step is moving from desktop applications to web-based ones, run on either cloud services, or on local server hardware. This allows a softer transition for both users and support, but as of 2019, the number of software products is still small; it is more suited for large organizations that provide the majority of their own tools anyway (usually outsourcing their development). For board design, I particularly like EasyEda as an example of this.
The only really helpful suggestion I can make, is to try and stop looking at the entire Microsoft/Windows-centric software ecosystem as
the way to do software business, and realize that there are other ways things can work, and work even better. Do not let Windows be your only tool, or the metric to which you compare everything else. You will find that there are better opportunities (healthier competition, ecosystem not controlled by a single vendor, and so on) and better models out there, even though their market caps are still much smaller than the Windows ecosystem's. Things change. There is no particular hurry, though; I suspect it takes a full generation for any change to really take hold.
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