OpenMediaVault VS Ombi

You might want to consider the previously mentioned MergerFS and SnapRAID, or MDADM and LVM for your setup. OpenMediaVault [https://www.openmediavault.org/ is a solid choice in this regard. Additionally, if you're planning to run something like Proxmox, you could look into deploying Starwind CVM on top of it. Pretty much like in this guide: https://www.starwindsoftware.com/resource-library/starwind-virtual-san-vsan-configuration-guide-for-proxmox-vsan-deployed-as-a-controller-virtual-machine-cvm/ .

You would better to install OMV instead. It's a ready to use fileserver solution with web interface.

So I'm working on a similar setup with an ancient desktop my in-laws were getting rid of. I installed OpenMediaVault directly to the hard drive (it's so old that I assume it wouldn't work too well as a hypervisor), with a 4TB external HDD attached. OMV supports Docker by means of a plug-in and I'm running a Jellyfin container with no issues at all. I'm still manually downloading everything to the HDD but *arr containers are my next step, as well as setting up a gluetun container to route all that through a VPN.

That is possible (it's automated to a certain extent). It also depends on the NAS OS. Unraid, for example, can work with drives of different sizes while using the largest one for parity. TrueNAS uses ZFS so you won't be able to just add a drive to your RAIDZ and expand it. There's also openmediavault: https://www.openmediavault.org/ that uses Linux Software RAID and you can add a new drive there but you can't combine drives of different sizes. And there's also Starwinds NAS that supports both Linux Software RAID and ZFS: https://www.starwindsoftware.com/san-and-nas. Plus, I would avoid SMR drives in RAID: https://nascompares.com/answer/list-of-wd-cmr-and-smr-hard-drives-hdd/

I'd put it like that: if you have a spare PC, then it's definitely worth trying. I would also look into openmediavault (minimal RAM needs): https://www.openmediavault.org/ and Starwinds NAS (supports both ZFS and Linux software RAID): https://www.starwindsoftware.com/san-and-nas

The Overseer part In truth, I'm less familiar with and it's full feature set, But at a quick glance it looks like it would be similar to ombi (https://ombi.io/). I know for a fact that you can set up OMBI to let users just type in stuff and it will grab it for them. I didn't like that and opted to manually approve requests.

Now add Ombi so that shared plex users have the ability to request content by themselves

Now pipe that all through ombi and you will live like a king! Also, don't forget to add your watchlist from plex to radarr and sonarr.

Ombi: Let users request both movies/tv shows from a simple web interface.

If what you're looking for is a request handled from the user's you give access to. Then you should check out Ombi. Ombi