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That probably exists somewhere as software, but probably not as ligatures in a font. That sounds cool.

Would definitely be limiting on which words you could make a readable ambigram though, because many ambigrams rely on letters that aren't one-to-one mappings (one letter becomes two, or letters between letters, etc.)

Fonts can be complicated. Using nonsense like [1] (specifically contextual alternates), you could have the glyph for the first letter of a word depend on the last letter. I don't think you could get that to work for all letters in an arbitrary length word, but making a font that works for all words shorter than say 20 characters should be doable.

[1] https://blog.glyphdrawing.club/font-with-built-in-syntax-hig...

This is a cool idea!