Re: Lies, damn lies and FOI
In my career, spanning Windows NT4 through 2016, I can remember all three times that I have actually approached Microsoft for support and on all occasions it was in the first year of release of the OS. There are so few issues that actually require escalation to Microsoft that cannot be dealt with by a competent support team.
If your database fluffs up, Microsoft couldn't care less unless it's a bug in their software. You probably would have found that diring the first 5 years of running the database on the platform.
Running on out of vendor support OS is completely safe if the network is correctly configured to isolate the OS and only permit access to the application. No internet access from/to the server blah blah. In fact, that 15 year old environment not get patched, poked and prodded all the time by external influences is likely to be rock solid.