Why do you consider this a problem?

We need more info. What model laptop, for starters?

Plex lets you add multiple servers.

The jellyfin app lets you switch, but maybe not use multiple servers simultaneously. I don’t have a second one I can add to test.

Actually, they have a demo server. Be right back.

Edit: nope, the android app only lets you connect to one at a time.

I don’t think jellyfin supports that either. I tried it a while back and only saw partial success.

Docker packs the whole application and its dependencies into a container, hence the name. You can run and delete that application as much as you want without affecting the host system. (But you should probably keep your media library and config outside the container, and use a bind mount. The setup documentation covers this.)

Back up anything you can’t afford to lose. Then run do-release-upgrade. You may need to use some option to allow it to go from LTS to non-LTS.

Use cfdisk and just edit the partitions.

Please note that if you do this without first resizing the filesystems on the partitions, you are very likely to lose data. You cannot safely shrink a mounted partition.

Edit: oh you mean booted from external media, not an online system. Use gparted. https://gparted.org/

VPN. Jellyfin is not intended for direct exposure to the Internet.

You should run it in docker anyway for convenience. A reverse proxy is optional, but I use traefik also for convenience (so that I can just use domain names on the same port, and so that it can automatically fetch certs).

Devuan is Debian with sysv.

Intel’s current corporate nonsense doesn’t affect the quality of existing products. They will continue to be supported under Linux and BSD for a long time.

Do you want x86-64 (amd64) or arm64? Those are two very different things.

Devuan supports arm64.

Or, relax your SBC restriction and get a mini-pc board like a NUC or N100, or similar embedded system. Even an HDMI stick PC.

Dell is not linux-first, but they do officially support Ubuntu for some models.

If you pass a whole raw disk, not virtualized, then TrueNAS should not complain. I don’t know if you can do that in proxmox, I haven’t tried.

Personally I’d get rid of TrueNAS. Even if docker is down, the VM with the data is still up and accessible over anything running on the VM, like scp via ssh.

If you’re adding drives with more capacity, why bother converting? Just create the new one, copy the data, then expand over the old disks.

Have backups for anything you can’t afford to lose, and be patient.

I don’t think you want two VPN services, I think you want one VPN service and plain network routing. Use the VPN server as the local gateway, and the VPN server routes that traffic up the tunnel.

You would be better served by asking questions in the existing post, instead of starting multiple new ones. Besides, these questions were already answered.

Usually the guy with a bunch of questions gets charged extra for being a nuisance while the guy is trying to work.

Didn’t need to, our developers work on Linux because that’s what their tooling uses.

Granted it’s either Ubuntu LTS or RHEL because of compliance, but they make it work. Unfortunately Linux is a second-class citizen to central IT, so when they make changes, they don’t really consider Linux users, they’re on their own.

A lot of enterprise security software has a Linux version, because a lot of servers run Linux, and they need to have the software for compliance. There is no shortage in that space.