Anytime Windows gets upgraded, there will always be the question of compatibility. Do my programs and applications work on the new platform? This has been becoming less and less of an issue in recent versions, but it is still a concern. This is especially a concern for those of us running software that dates back to XP or (cringe) before. I cannot speak to your specific applications, but my point is that it’s something you need to plan around. Before you jump in and start upgrading everyone to Windows 10, maybe do one or two machines just to see what works and what doesn't.
I think the biggest challenge with this update facing Microsoft customers is the user interface, how things look and how common actions are performed. It’s much less jarring for those brave souls who already moved from 7 to 8 or 8.1. But even then, there are some major changes and you’re going to need to plan for training your staff on how to use it.
Microsoft has a history of alternating between really good and really bad Windows releases, and in my opinion and experience with Windows 10, that rule definitely holds up. My recommendation to you would be to definitely get a plan in place for making the move before you start having to pay for the upgrades next July.
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