> Personally, I don't think a machine that has that limited storage ought to be 
> upgraded using apt from one Debian stable release to another.

It's not the machine but the partition. One can set up Debian to use a separate 
partition for the home directory. When the root partition on a SSD has 20 GB 
(about the size I think all guides I found on this suggest or use in their 
example) which should be large enough and the upgrade claims it needs 5 GB and 
actually needs 7 GB that can obviously be a problem.

> it is not supported to arbitrarily break apt updates up like that

...which is why this an issue for a new functionality rather than already 
existing. It doesn't have to be arbitrary.

It's common sense to break up GB-sized downloads into several steps. Last 
upgrade failed due to disk space issues; this upgrade I had to clean caches 
during the upgrade as workaround; I'm sure many have this problem and even if 
it's rare it would be best to have upgrades run smoothly and reliably (such as 
checking remaining disk space throughout the upgrade and adjusting 
accordingly). Those are not several upgrade but one upgrade that downloads not 
once initially but several times and cleans up the caches after each step.

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