I have a couple of thoughts about this.
Firstly, I thought sans-serif typefaces were encouraged for digital media because they read better than serif fonts. But now that high pixel density displays have permeated the market, this might be a moot point.
On another note, I wonder how much of the hate TNR gets stems from its ubiquity for having been installed on almost all personal computers for the past n decades.
Paganis are beautifully designed cars, but the labelling of buttons and toggles inside the center console look cheap (IMO) because their font seems straight out of a quickly made flyer designed by bored teacher who just discovered Word Art.
If I recall, Watson was fed the whole text of the answer as soon as the other contestants could see it. Personally, I thought it would be fairer to have it do speech-to-text and/or OCR to level the playing field.
But I suppose these constraints are just targeting the machine's input mechanism and not its actual reasoning ability once the answer is read. I'm curious how Watson at the time could handle a particular category that Ken dominated: "Initials to Roman Numerals to Numbers" [1]