While I don't regret my career decisions, one thing that always comes back is the thought: What if I had doubled down on the Windows API and C++. I don't see m

While I don't regret my career decisions, one thing that always comes back is the thought: What if I had doubled down on the Windows API and C++. I don't see many job openings for those types of jobs, but I would have had an incredibly stable platform for the past 25 years. If you wrote a service for Windows in the early 2000s, it seems like it wouldn't be that much work keeping it running today. I have seen examples of companies managing to lock their software to Windows Server 2008 by accident, so there is some room for failure, but that might very well just be incompetence.