Retroactive VS wireguard-windows

No need to keep Mojave to run iTunes — iTunes can be run on newer macOS, by using Retroactive [1] to patch it.

Regarding running a newer macOS on older hardware, check out OCLP [1] — do make sure you make full backups and have a working recovery plan before trying anything with OCLP though. I know that might sound somewhat obvious to a lot of folk, but you'd be surprised at the amount of folk that jump in and try OCLP on their main system without any backup plan.

Note that are some gotchas re installing OCLP on some older h/w, and it will help to read up on possible issues before wading in. e.g. during installation it might be necessary to use a wired keyboard and mouse, via a USB hub, until the installation is done, you might also need a wired network connection during install, similarly. Depends on h/w (I've not patched MacBooks myself, yet). Once the patcher is done, these should not be needed anymore.

Official support for OCLP is only via Discord — but there is a very active unofficial peer/user support group on FB [3]

HTH!

[1] https://github.com/cormiertyshawn895/Retroactive

[2] https://dortania.github.io/OpenCore-Legacy-Patcher/

[3] https://www.facebook.com/groups/opencoreprojectlegacy

Or use Retroactive.

That said, my 2020 Mac Mini M1 also works great with the USB iPods - I used an app called Retroactive to get iTunes 11.4, which works fabulously to load my iPods. Can't say how well it works with the Firewire iPods, as I don't have all the requisite Thunderbolt adapters to make it work.

There's a project called Retroactive https://github.com/cormiertyshawn895/Retroactive/ that lets you install iTunes 10-12 on Catalina and newer OS. You could do that and still keep your playlists, etc.

you can run Aperture on newer Macs https://github.com/cormiertyshawn895/Retroactive/ just in case you want to check.

Create a WireGuard config in the AirVPN cliant area. Install the WireGuard app in Windows. Import the config file.

https://www.wireguard.com/install/ is the wireguard installer for windows. I'm not sure where it stores its configuration files on windows, but I'm sure that's documented on their website somewhere. Then you can configure it according to this wiki article https://wiki.archlinux.org/title/WireGuard (yes it's for Linux, but wireguard works basically the same whether on Windows or Linux)

It seems the current official WireGuard Windows client, version 0.5.3, hasn't been updated in quite some time now. The GitHub repo shows no changes this year.

Again, have you tried your configs on wireguard application (link below) https://www.wireguard.com/install/

If this [1] is what you are using then create an issue on Github describing your setup, the issue and detailed steps to reproduce it. It appears they have 43 contributors so hopefully someone will have ideas.

[1] - https://github.com/WireGuard/wireguard-windows