@LB, I'll take the liberty of grading you
|-Different words are spelled the same (do read, has read) or similarly (of, off, on, one)|
1/2. Somewhat of a problem, but that's the price of having a lot of short words. Would you rather have most common words be 2-3 syllables long?
|-Different words are pronounced the same/similar (there, their, they're, two, to, too, its, it's)|
|-Complex rules with many exceptions and even exceptions to the exceptions, which generally make it easier to just memorize thousands of words than memorize the rules|
0. You're being a bit vague, is this about pronunciations?
|-Many words which are from other languages and have been adopted into English unchanged|
0. You complained just a moment ago about how bad it is that pineapple was adopted and changed. Make up your mind. And, why is this a problem either way?
|-Highly contextual grammar|
0. Is this about English being more analytic then synthetic? Are you aware that the other option is to have longer words that mean a bunch of things and have sentences where a whole bunch of things is implied.
|-Many cultural expressions|
1/2. Kind of annoying, but that's sort of the difference between a living and a dead language.
|-Many words have no opposites|
0. You mean how there is no "vincible" for "invincible" (apparently there is)? As with foreign words, why is this a problem exactly?
|-Seemingly related words have completely irrelevant spelling and usage|
1/2. irrelevant? I assume you meant unrelated. How much words are related is actually a thing I like the most about my (not English) language. But then this is kind of the same as the point of being an analytic vs synthetic language...
|-Ease of ambiguity with sentences, especially with pronouns|
-Difficult to properly express certain ideas in a compressed format (they took the test; one person or multiple people?)
1, but that's one point.
|-Many words do not use the roots and bases you mention|
-Many changes to words are irregular (person, people)
-Multiple different kinds of plural/possessive (person, people, persons, peoples, person's, people's, persons', peoples')
1. These are kind of the same point though. And I doubt there exists a natural language for which this would not be true....
So that adds up to 4.5/13 = a sad smiley face :(. Seriously though, you could fix/change most of this in English 2.0, but I'm not sure you'd actually want to speak it.