2. I've also started to consider the Raspberry Pi route, to the point
that over the last few days I've been looking at what would be involved.
For something like $200 or a little more, I can get: a Raspberry Pi 4
kit (without USB mouse or keyboard--I have extras) with enclosure, power
supply, 4GB of RAM (double what my Netgear NAS has), 64GB SD card, and
HDMI cable; a low-end 2TB portable USB 3 drive; and a USB 3 hub to make
sure that the drive (and possible future drives) don't overwhelm the
power supply.

That's way too much. No need for the disk, nor hub. Just leave the files on the NAS. The NAS is designed to serve files. Set up LMS on the Pi, mount the NAS to it, and scan the library from the NAS directly. I've been doing this with a ReadyNAS Duo v2 for a while.

You mentioned SSL and https as likely future issues with the old Netgear
systems (like mine with its current OS). I believe that Netgear's OS6
supports https in at least some ways (although it has to be enabled).
For example, See:
https://kb.netgear.com/23100/How-do-I-configure-HTTPS-HTTP-with-SSL-encryption-settings-on-my-ReadyNAS-OS-6-storage-system
Would ReadyNAS OS 6.x likely be adequate for LMS and its plugins over
the next several years, permit me to hold off on a switch to something
else, such as a Raspberry Pi? Or would a current switch to a Raspberry
Pi seem more sensible even for someone who has used almost no
command-line interfaces since switching from MS-DOS to Windows circa
1993?

I usually recommend using piCorePlayer in situations like yours. Because it's super simple. No command line experience should be required.

--

Michael
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