Having just upgraded to Windows 10 version 1903, I must admit that Microsoft has made the process much less annoying. All of my data, most of my settings - and surprisingly, all of my drivers - were retained. Some drivers did appear to have been "repaired" by Windows, as unnecessary additional driver components had been reinstalled/re-enabled, but my older drivers haven't been updated (e.g. I use a custom Bluetooth driver which enables the aptX codec). This is the first feature update that hasn't trashed my Windows 10 install. A range of minor, and seemingly random, changes did occur, including some of my custom Registry tweaks being removed, 8Gadgetpack requiring a repair, and of course, the telemetry being completely re-enabled. Everything is performing well, drive space is the same after a cleanup, and there are no new annoyances to report. So if you were holding off on upgrading, now appears to be a good time to do it.