I realize this is a humor article, but... well, okay, I think the questions are asked often enough seriously to warrant answer. I'm NOT a linguist or English major, but this is what I've picked up over a lifetime of using and learning about it as a native speaker:
1. English is a strange hybrid langauage, in that where most languages have a single 'root language'-- like Spanish and French are latin-based-- English is based on both Latin and Germanic roots. This is why sometimes English sentence structure follows German very closely,a nd other times it does not. As for things like now/know/no and such... well, that's the nature of language. It evolves, and in doing so, develops strange rules. English, by its largely hybrid nature and English-speakers' tendencies to 'borrow' words and such, develops a lot of idicyncracies, but you'll find things like this in most languages, I'm told.
2. A semi-colon is used to link two independent phrases together when they're related to each other. It essentially takes the place of a period between two sentences to show that one thought is related to the next. Similarly, it also behaves as a conjunction like 'and' or ', but' with the context of which relationship it implies given within the sentences. A dash(--) can also be used in a semicolon's place-- though a dash can allso be used in place of a comma to form an appositive-- an interjected fragment that gives more explanation of a concept-- just like I'm using here. Colons are quite different; they're used when one phrase cannot stand on its own, or to introduce a list.(Not the semi-colon here-- I could have just as easily said "Colons are quite different. They're used when one phrase cannot stand on its own, or to introduce a list." or "Colons are quite different, because they're used when one phrase cannot stand on its own, or to introduce a list." I chose to use a colon because the relationship is implied and it's my stylistic choice.) The major thing to remember is that with a colon, the second phrase won't stand on its own as a proper sentence. A semi-colon is also sometimes used instead of a comma to delimit a list.
3. You captitalize when: it's the start of a sentence, or you have a proper noun. "I need to see the doctor, so I made an appointment with Doctor Smith"... in this case, the first time, I'm using a general noun denoting the general concept of a doctor-- in the second, I'm referencing a specific doctor, and thus I capitalize, because it is being used as a title, part of a proper noun. Sometimes in colloquial writing, you'll see people capitalize in Places That Do Not Seem Appropriate. Sometimes this is being done to put emphasis on particular words by treating them as a proper noun, but it is not correct English per se.
3b. You don't start a sentence with And, But, Because, Which, or a number of other words of the sort because they are conjunctions. They are designed to link an incomplete sentence(fragment) to a complete one. If your sentence is complete on its own, you don't need one. If it isn't, then you need to put a complete sentence on the other side of the conjunction.
4. Whom is the prepositional form of Who, if I recall correctly. "Who owns this dog?" "To whom does this dog belong?" Tha'ts a very contrived example, but it illustrates the point. A better one might be that it's actually incorrect to say "Who does this dog belong to?" as many people do. 'Whom' is the correct form to use in this case.
4b. Contractions are easy, via the following exercise: Say "It is Monday." Now say it faster. Faster. Faster. Eventually it'll sound like "It's Monday". Eventually this colloquialism becomes common, and then becomes proper. I refer you to #1-- languages evolve. Except for dead languages.
I award myself the "Answered a Humor Question Seriously" Nerd Award. Yoiks, and away!