I think the problem though is that language is ever-shifting. This leads to insanely stupid grammar nazi arguments over things like "Who does this belong to?"

I think the problem though is that language is ever-shifting. This leads to insanely stupid grammar nazi arguments over things like "Who does this belong to?" vs "To whom does this belong?" And that argument has been going on for at least a century. Regarding glyphs you have a number of problems. These include phonetic shifts. So for example, in English we have a word like courtyard. This is a compound word with two components, court (from French) and yard (from Old English). Both of these come from the same PIE root. Now this isn't too bad with court and yard, but let's look phonemes of another sort: what PIE kw- vs gw-. gw- became qu in Old English (hence words like queen), while kw (which becomes qu in the Romance languages) becomes wh (what, where, whorf, whirl). This is still arguably separate from a w sound as most people I know pronounce where slightly differently from wear. Combine this with the fact that we have lost letters (thorn and eth, primarily) which refer to distinct phonemes which we now use th for. To come up with an optimal language, I think you'd have to make it fully prescriptive and heavily spec'd out (like computer languages are) but this isn't the way human language works. I suppose someone, probably me, has to point this out, and if you didn't get the subtle jab at discussions of pronoun cases, please re-read this sentence, slowly.