You can upgrade, but you need to do this in a few steps...
Make a backup of your router's current settings
Reset the device to defaults (this is necessary later anyway, but might as well do it now)
Upgrade to 19.07.10 -- do not keep settings during the upgrade
Upgrade to 21.02.5 -- again, do not keep settings during the upgrade.
During the upgrade from 19 > 21, you'll see a warning about an unsupported image format... just make sure that you've downloaded the correct sysupgrade image file and that the checksum matches what's on the website... as long as those are okay, you can force the upgrade. This is because the device transitioned from ar71xx to ath79 target architectures.
Upgrade to 22.03.3 -- don't keep settings, just like before.
configure your router. Do not attempt to restore your old config backup... it is not compatible. But you can use it as a human readable reference if you need it.
Upgrade to 19.07.10: there is no NAND image for the AR300M, only NOR (my current version is NAND). After flashing: what version is booted: NAND or NOR? When I do the later upgrade steps, can I change from NOR to NAND?
Upgrade to 19.07.10: do I upgrade within luci or uboot?
Upgrade to 21.02.5 and 22.03.3: I assume I can upgrade within luci. Correct?
I've collected and reviewed all OpenWRT information regarding flashing the AR300M. Last but not least I decided to go the following route: flashing via u-boot (as recommended on the wiki page) with the 22.03.3 factory image. This 1-step upgrade was successfull.