"It’s almost impossible to feel like part of a community if you’re not highly proficient in the language. Even non-native speakers who are fluent enough to read posts in their second or third languages often aren’t comfortable enough to write in them." Wow, this is true! I am brazilian and you have no idea how much effort I put in writing every single comment here on HN. And the longer de comment is, the more stupid…
There is a real brutal grammar nazi trend I've been seeing recently on various sites - apparently, someone gets a buzz of self entitled superiority off of correcting someones grammar mistakes. Personally? I think English is insanely stupid, inefficient, and dumb. I speak it because I have to, not because I want to, because everyone else does it. If you think trying to get breakout success in a market with, say, a sof…
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.