Its not done too bad though - a 13 year lifecycle for an operating system is a fair innings .Mainstream support has already been discontinued for 4 years and its not like your PC will stop working on April 9th but there are dangers to use it after then if you don't upgrade - no more plugging of any remaining holes and by microsoft and also other things like Antivirus may not be updated by the Antivirus companies. That said if you are using an up to date web browser and are careful at home you should be fine for a bit longer yet.
I am not (fortunately), but some of my colleagues are still supporting machines that run Windows NT. Too important to turn off, too flaky to try and update, too difficult to virtualize (has been tried previously).
Arm + leg and probably some other body parts. When I left my last job (~5 years ago) a council down south (could have been Croydon) had over 400 DOS-based critical applications.
I take that and raise it with Microsoft Mail on Netware 3.1... Or Lotus Notes on anything. The kids these days do not know how lucky they are with Exchange 2007 on Windows 2003/8. Although Ex2013 on W2012 with lots of Powershell will be fun for them to learn