kjstech
Hi Keith.
Happy to help, I hear frustration in your feedback, but missing a lot of details that I might help with.
Some initial thoughts, feel free to engage with specifics if you would like help.
1) Once we work through your issues, I'm confident we will get you to were the vast majority of devices are today, installing updates and getting the security, end user functionality, and quality improvements that come with them. There are literally millions of devices that do this every day, consumer, slam business and large enterprise. You did not indicate with SKU you are using, but I'll assume pro is you are focused on the 18 month security servicing for each release.
2) You forecast that it will take you more than 18 months to roll out 1903 to your organization, but no details on what is limiting that velocity. I work with many enterprise customers ( other than Microsoft ) who update 1000s of devices weekly, some even more. What are the limits that you running into and effecting that velocity?
3) Just to make sure , though I think you know this, for Pro SKU, we provide security updates for 18 months. So if you choose , you can update devices as slowly as <1 / year, and still stay security patch current, you do not have to update 2/year. The customer trend I do see is that once you get process in place to update once every 12 months, then updating more frequently, if you choose is incremental. Most of the change management is completed in getting to update more frequent than every 3-4 years, ie once per year.
4) Do you have specific issues that have prevented you from updating those devices on 1703? How do you manage updates?
5) We have updated millions of older machines that started life on Windows 7 , and now are now extending their useful life with improved security and new functionality with Windows 10, and the Windows 10 feature updates. Windows 10 will certainly outlive the HW, but while it does so, it is extending the life of that HW.
6) 1607 devices that wont update.
Tell me more? Have you check free diskspace? This is one of the most common sources of update failures, lacking free space to download and install the updates. Do you have 3rd party encryption and security products that might be conflicting? Many then, fewer today still, required you to first uninstall, update the 3rd party tools before the update, though I would expect you would have worked through this with other devices that did update, so check disk space. Have you used the Setup Diag tool?
John