John, I treat emoticons as words. I apply them the same as the question mark in 3. If it applies to a specific sentence, I place it within the sentence at the appropriate location, immediately following the expression that is being emoted. If the emoticon applies to a broader aspect of the message than a single phrase or sentence, I place it following the entire expression. In this case it stands alone and needs no independent punctuation. A phrase can be emoted :-), and there's no reason multiple emoters cannot reside within the same sentence (:0>. This is common with new technology, that we come upon specific applications that fall outside the existing rules, and we must interpret the rules to fit the application. That interpretation can only be done well if we have an understanding of the reasoning behind the rules. <VBG> (Sort of like interpreting bylaws ;-).)
Because punctuation is frequently used to create the emoticon, sometimes a little creativity may be called for to make the expression clear. Is the bylaws smirk sufficiently clear? Of course, given the free form media we are expressing ourselves in here, we could be like vanity plates, and deliberately be cryptic, just for the fun of it! ÿþ> <><> <> <> <><> < HAHAHAHAHASNORK