I have not tested it yet, but it seems that it handles dependencies, something that you would have to do manually with apt download.

From what I understand it simulates a full apt command on the offline machine, but instead of downloading anything (it can’t) an instructions file is generated. This file is then loaded on an online machine, and used to download everything needed for the offline one. Then the downloaded packages are transferred in bulk to the offline machine, and installed there.

You can find an usage example here: https://manpages.debian.org/bookworm/apt-offline/apt-offline.8.en.html#Sequence

Problem is, Im not on a linux machine, to perform any downloads for the linux machine that is offline only. So unless its all in one to grab and install. It wouldnt work.

But I must have added a bunch of stuff years ago, because I grabbed the default Stable file from Staging. The linux version. It ran fine. Still. Shame there wasnt anything easier, if the dependencies werent already in place. The reason I even tried it was, I was half asleep and thought I grabbed the Windows portable version >_>
When I transferred the files I had over, I was like....oh well, guess ill test it.

Thanks all the same folks. Now I have a useful DOS pc, instead of a dust collector.

Nope, problem is you are forcing yourself to use a system while at the same time having decided that you hate it.

You should drop Linux from this machine and install Windows (any version) instead.

For the download, you don't need a physical linux machine. You can, for example:
* Install linux in a VM, then do the download there.
* Use WSL (which, if it's WSL2, is actually a Linux VM) and do the download there.

I recommend using the same distribution for the VM/WSL that you're using on the target computer. It doesn't necessarily need to be the same architecture (but do check to see whether the version of Linux on the computer is 32-bit or 64-bit, so that you download the correct files).

Thanks, but those are not viable options for the machines I have.

Why not?

My computers are set up in a way, that even when obsolete, I can still use them for something. Like the dos machine I just set up. Plus I really dont wanna waste space to clone that particular machine. When it dies, it dies.

...that and Im barely motivated to tinker at present xD

You can't just install a linux VM on a modern computer with internet access, use apt-offline (or equivalent) to download the files to the virtual machine, then transfer them (via USB or or optical media) to the old computer?

He doesn't even need to mess about with VMs. Just a live USB Linux distro iso would do. Burn Ubuntu on a usb stick, and voila and boot into it to mess about. Easy peasy.

But he's not interested at all. Even though he'd have to jump through similar hoops on Winblows.

Linux is not for everyone, it seems.