I'm stuck in XP Pro / Windows Server 2003 land. Why? Because I own business software that is specific to my trade. The software I have is still more than adequate for me. The cost of upgrading hardware pales in comparison to the cost of the same or comparable (not a lot of it out there) software that will run on modern OS's. On top of that the newer software is not owned, you pay to use it for continual monthly or yearly fees.
Do not know what software or business you run, but have you ever performed a risk assessment? I’ve seen a fair share of great financial losses due to EOL software

