Regarding upgrading, there are reasons to upgrade. In no particular order:
* To maintain support. Vendors cannot support everything under the sun. It's just not feasible. Time moves on, new stuff comes out, and the old stuff settles into history. It's getting more and more difficult to find support for things such as Windows 7, Windows Vista, And Windows XP. On the server side that would be Windows Server 2008 R2, Windows Server 2008, and Windows Server 2003. I currently support about half a dozen Windows Server 2003 installations between two clients. I have been begging those clients to upgrade for years now. One is finally moving forward. The other shows no sign of doing anything. How much longer do any of you think I can keep Windows Server 2003 going? One day in the not distant future, that client's Server 2003 installation will blow up or not be able to do something and he'll be stuck. And my only answer will be to find a good bankruptcy lawyer in his area. He's already expecting me to find solutions for printing because the brand-new printer he just bought doesn't have 2003/XP drivers so that means using the generic driver which means no color and no front-and-back printing.
* Efficiency. Windows Server 2003 was wonderful back in the day. And I miss, with all my heart, Windows NT 4.0. I still have a copy running in a VMWare virtual machine because I'm nostalgic like that. But there is no way I would support that stuff anymore for a new client. It's horribly inefficient from every angle you can imagine from no support for USB to no way to managing power consumption like what we have today.
While I certainly do empathize and sympathize with being told yet again it's time to upgrade, proper IT scheduling is what will save your bacon and your wallet. The only real issues I see are from the DIY crowd. It may be time to ask for some help. My SQL Server 2012 to 2016 upgrades have gone without a hitch every single time. But then again, I live and breathe SQL Server every day.
JamesNT
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