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Blocky fonts could just be Yahoo falling back to older fonts as it finds the Windows/MacOS fonts not installed on the local system. The easiest thing you could do to verify this is install the mscorefonts (the way to install it changes every few years, so you'll need to search it).
You probably don't need the ms core fonts exactly, as long as there are compatible replacements installed. But that's a simple enough starting point, agreed.
Correct, the mscorefonts may be a little overkill, but it would be the quickest solution. My guess is that Debian's default fonts "aren't up to par", so they could also download and install other fonts and use them as the default san-serif font, but unless they got lucky it could take longer than just installing the fonts their father knows and loves.