In my experience that's not how it goes. I started on Windows 7 and still have a laptop with a working setup…however IE no longer works and there have been several security updates which kill the DICE connection.
VIDA 2014D was an absolute pain to get working - it works (mostly) on my Win 7 and Win 10 laptops, but there are 2 other laptops which I could not get a working install on. I don't know why. Windows 10 I now have to use Chrome with workarounds, or Edge in IE mode which usually works.
My point is that even if you bought a working setup, unless you never updated it (and I suspect even then), the system will probably need tweaking in the future to keep it running. Just like the Volvos themselves, ongoing maintenance is required.
I bought an ebay DICE which happens to work perfectly, and have plenty of experience muddling through installation guides and typical issues. I even have a few bootable USB based systems which work if you have plenty of patience - they're very slow. You're welcome to pick my brains or test using my DICE for comparisons etc. I'm on Northern Beaches (home) or Western Suburbs (work).
Don't get me wrong - I'd like an install which just works out of the box too. That's just unrealistic in my experience…