Windows 10 is just not well suited for machines that have any kind of custom services for business installed unless you like tracking down all of the software which fails to migrate for undisclosed reasons at every biannual update.
Just had to deal with a machine that received the 1809 update last Friday. The absolute and only thing the owner knows that he received from the update was a need to have printing on one of his machine restored. The printer wasn't uninstalled, it migrated fine. The printer port, a standard virtual printer port for USB provided by Microsoft, was not migrated, so the printer could only be used in offline mode, and finally the custom software that his printer needs to handle print jobs also failed to migrate. Where is the value in the 1809, or any of the previous updates for this customer? For business machines, most if not all of these feature pushes are pretty useless and can be guaranteed to be as trouble free as having a mechanic take the engine in your car apart twice a year and then reassemble it. For a machine that is otherwise fine, all you're doing is increasing the chances of something unwanted happening to it.
Is part of this nonsense about breaking machines to drive future sales?