There are a number of things which I don't like about English grammatical rules. The one I want to address here is the nested quotation, which is not only confusing but unwieldy. Consider the following example:
Adam said, "I like apples."
What if this was part of a narrated story?
Beth said, "Adam said, 'I like apples.'"
And if I nest that again...
Carl said, "Beth said, 'Adam said, "I like apples."'"
Obviously, anything this complicated should be rewritten in any case (Carl said, "Beth said, 'Adam said that he likes apples.'"), but putting that aside, it really bothers me that I cannot just copy and paste a piece of text, wrap quotations around it, and be done with the change. If you notice carefully, the rules of English require the outer-most pair of quotation marks be double quotes ("), and each nesting from then on alternate between double quotes and single quotes. For the copy-and-paste usage case I just mentioned, this means all the quotation marks needs to be switched, which is extremely annoying.
Despite this asinine rule, I can actually see the reason: the inability to distinguish between nested quotes and sequential quotes. Compare:
Carl said "Beth said 'This note reads "This note can talk."' I like talking notes."
Carl said "Beth said "This note reads "This note can talk."" I like talking notes."
The first sentence is Carl quoting Beth who is quoting a talking note. The second can mean the same thing, but the ambiguous quotation can also mean Carl quotes Beth, then adding his own comment, and someone else replying. In proper quotation, this latter meaning should be:
Carl said, "Beth said, 'This note reads.' This note can talk?" "I like talking notes."
It can be argued that the alternating quotation, therefore, makes the meaning of nested quotations clearer (with some excuses as to other improper punctuation, of course).
The main problem with the quotation marks is that the starting and ending marks are the same. By nesting the quotation marks, inner quotes will never be "accidentally" terminated by outer quotes. More modern character encodings solve this problem with using different characters for beginning and ending quotes. You can look at the Wikipedia page to see how to type the different ones - although most word processors will do that for you automatically anyway. With computers, the problem is compounded by the starting and ending single quotes doubling (or as it were, tripling) as the apostrophe as well. This is only really a problem for contractions at the beginning of words though, such as "'cause", which could be interpreted as a starting quote. I'm not sure how word processors deal with this.
Personally, I prefer to stick with ASCII. Since I quote a large amount of emails and chats in my journal, and the emails and chat themselves very often quote other things, I can't be bothered to switch the quotation marks back and forth. This sometimes does cause me a little more comprehension time, but compared to the time I would have wasted on changing punctuation, it's not a big deal.
How do you use quotation marks?