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Might be worth centralizing the list of available thumbnail files using some function, and then using that in both get_thumbnail() and in here. Maybe something that supplies the filename and the 1x/2x/etc. This will also help us scale up thumbnails for higher-res displays down the road.

Can you show me an example of how these paths end up looking? The before/after? I feel like there's got to be another way to do what we want to do here.

Can you add -> None for each of these, so we can do type checking as part of tests?

Just for alignment purposes, we can prefix all these with f, even if we're not putting in any format strings.
There's no difference to Python. A format string that doesn't format just becomes a string.

>>> import dis
>>> def foo():
...     return (
...         'test'
...         f'{hi}'
...         'bar'
...     )
...
>>> def bar():
...     return (
...         f'test'
...         f'{hi}'
...         f'bar'
...     )
...
>>> dis.dis(foo) == dis.dis(bar)
True

Add a blank line between these two.

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Missing trailing comma.

We can just use attachment, since we have that locally.

lstrip() isn't safe. It doesn't remove a prefix. It removes any leading characters found in the provided string. So, any characters listed in site_media_url will be removed from the beginning of the URL.
Ideally we'd use removeprefix(), but that's only in 3.9+. So you'd instead need to do:

if t.startswith(site_media_url):
    t = t[len(site_media_url):]


Or maybe assert that it starts with it? Or skip/log if it doesn't?

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