Internet, Web, and Other Post-Watergate Concerns

Q. My question is, is there any standard for the usage of emoticons? In particular, is there an accepted practice for the use of emoticons that include an opening or closing parenthesis as the final token within a set of parentheses? Should I (1) incorporate the emoticon into the closing of the parentheses (giving a dual purpose to the closing parenthesis, such as in this case. :-) (2) simply leave the emoticon up against the closing parenthesis, ignoring the bizarre visual effect of the doubled closing parenthesis (as I am doing here, producing a doubled-chin effect :-)) (3) put a space or two between the emoticon and the closing parenthesis (like this: :-) ) (4) or avoid the situation by using a different emoticon (Some emoticons are similar. :-D), placing the emoticon elsewhere, or doing without it (i.e., reword to avoid awkwardness)?

Q. According to CMOS 7.73, computer menu items are capitalized. The editors I work with insist that a menu item from a specific website (such as yours) should also be placed in quotation marks. Here’s an example: Click on “About the Manual” to learn about changes made to the recent edition. I think the quotation marks are unnecessary. What do you think?

Q. The CMOS standard is to paginate front matter with lowercase roman numerals, and then use arabic numerals in the text and back matter. This causes a problem when I publish an electronic book in PDF format. PDF numbers the book sequentially, ignoring the different numbering of the front matter. Reading between the lines in CMOS 16, I have come to believe that numbering the front matter separately is a historical artifact. When the text was written first, followed by the front and back matter, and all were done mechanically, one could not number everything sequentially from the title page. In these electronic times, though, sequential numbering takes seconds, literally. Why then use a separate numbering scheme for front matter?

Q. In your bibliography, do you type in your websites so they will be “active”?

Q. When publishing a web address in a print publication, do you recommend underlining it (as it would appear on the web), bolding it, or doing nothing? Is one way better than another when the web address is at the end of the sentence (thus, followed by a period)? Example: For more information, visit www.chicagomanualofstyle.org.

Q. According to The Chicago Manual of Style, Wikipedia should be italicized, but YouTube shouldn’t. Because Wikipedia is classier?

Q. We are debating in our office how to refer to our website when the URL appears at the beginning of the sentence. Would we capitalize the first letter (i.e., Www.abcd.com [address changed for this forum]) or not (i.e., www.abcd.com)? Are there any conventions around dropping the “www” (i.e., abcd.com)? If so, would we capitalize the first letter (i.e., Abcd.com)? What about all caps (i.e., ABCD.COM or WWW.ABCD.COM)?