(2) Are you saying neither computer will reinstall when you click "Update Now" at...
https://www.microsoft.com/en-us/software-download/windows10
Download Windows 10 -- Always the latest released version, currently 1909
That would constitute an over-install of 1909 keeping all files, settings & apps. But - as you've got such instability - definitely ensure you backup important files & downloads to external media first. Also, it might be best to make a USB Installation drive with which to do the over-install. If it fails, you'll be able to try a clean install with it, instead.
FYI
- Both 1903 and 1909 share a common set of system files.
The current version of the 1909 MCT Tool or the stand-alone 1909 iso is based on 1903(not uniquely 1909) even though it does include 1909 bits and will clean install 1909(1909 is a simple, small update from 1903 and included in the bits during setup and final install prior to first logon)
What does the above mean and what has previously been seen?
- Use of the MCT created media(USB/DVD or ISO) or stand-alone downloaded ISO[using a different browser UA string or Win7/8x device] or online 'Upgrade now) with 1903 bits(setup.exe is 18362, not 18363) used to perform an in-place upgrade(i.e. over-the-top-install) may not(and has not in reported cases) provide the all encompassing option 'Keep all files, settings, and apps' option => when the device is already at 1909(18363) - the target o/s on the system is newer than the o/s on the created MCT or ISO.
-i.e. 'Keep all files, settings, and apps' is a version specific option - same version to be available.
In the past, the MCT created media and/or ISO was uniquely version specific to the current feature/major update, this time around it was released with 1903 bits and the 1909 upgrade bits.
Thus, over-the-top install keeping 'everything' won't be available(grayed-out), only 'Keep personal files' and 'Keep Nothing'.