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MyOutfitIsVague parent
Linux has to install somewhere, and it needs a filesystem that supports POSIX permissions, so you need a partition formatted for it. If NTFS is taking up the entire drive and can't be shrunk, where does Linux install?

You can't do this all on the same drive, because you need a place to copy the documents directory to. You need to delete the NTFS partition to create the place to copy the files to, but by the time you've done that, the Documents are inaccessible. You could do it in memory, feasibly, if you create a RAMdisk and are lucky enough to have enough memory for all your documents, but then you're still gambling on not running out of memory during the install.

So it is possible to copy the documents on the same device, and it's possible to even automate the process, but it's not possible to do it reliably or safely, and the reliability is so low that it's not worth even offering the possibility. If somebody has a handful of gigabytes of documents, it's already a nonstarter. To be safe you'd demand the user make a backup onto another device anyway, in which case they might as well do that and then copy the files into a fresh install themselves


TheBicPen
I imagine it wouldn't be that hard to 1) check the size of the documents directory and the existing NTFS partition on windows and 2) if the existing partition is < (1/2 the disk size - the size of the Linux installation), give the user the option to shrink the partition and copy the relevant files over to the new /home. This is assuming the tool is going to install a dual-boot configuration anyway, at which point this isn't significantly more work. If the idea is to completely overwrite the existing installation then this would make the process significantly more complicated. But I imagine that for a tool intended for less-technical users, dual-boot installation is the way to go to give them assurance that their existing setup will continue to work.
MyOutfitIsVague OP
For a dual boot configuration, you might as well not copy anything over. You'd be better off mounting the Windows partition in the Linux install. There's not a great reason to dual-boot for non-technical users, though. The point is to end up on a system that works for them, not to have one that works for them and a derelict system that they don't know how to remove, and that can destroy their dual-boot setup if MS decides to push an update that overwrites the boot loader, leaving them unable to access the Linux install.

It's not just shrinking and copying over to the new `/home` because of the locality of the data. If your NTFS partition is taking the entirety of the disk (minus EFI and system partitions), shrinking it will then make it take up the first X% of the disk. Then you have to make the linux installation on the last (100-X)% of the disk, copy the files over, and then when you delete the NTFS partition, your Linux filesystem is on the last half of the disk with a big blank unallocated area on the beginning. BTRFS or LVM2 could help a little bit there, but that's far from ideal in any case.

Probably the best approach would be to shrink NTFS, create a new partition at the end of at least the right size, copy the files over, then wipe the NTFS partition, install Linux as the first partition (after system/EFI and such), then copy the files into the user's home, and then remove the documents partition. That's still not super reliable, though. You are at the mercy of your documents sizes, filesystem fragmentation (remember, even if your filesystem is mostly empty, you might not be able to shrink if fragmentation is in a bad place. You could defrag, but then the install time can balloon up many hours for the defrag process alone, just to shrink a filesystem that you're going to delete anyway), how big the Linux install will end up being, and many other factors. You'd have a lot of people who simply can't copy their documents over on install who will be simply SOL. I can't think of a situation where this kind of thing wouldn't be better served by just telling the user to backup their documents to a USB drive and move them back afterward, because many people are going to have to do that anyway.

charcircuit
One option you didn't mention was syncing everything to the cloud, and then redownloading it all.
MyOutfitIsVague OP
That's effectively the same as my last sentence.

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