1. Should political bloggers and online pundits be regulated by the FEC and bound by campaign finance laws or should the status quo remain?Quick answer to this one which I'll expand on later. EVERYONE is bound by campaign finance laws and regulated by the FEC when it comes to campaign donations. Whether I have a blog or not, there is a limit to how much money I can donate to a candidate. It seems to me that the problem that arises in this very good question is how to evaluate blogs and online pundits from a campaign donation type of standpoint.
2. Is this potentially a first amendment violation, equivalent to telling someone they can't wear a political button or talk up their favorite candidate at a cocktail party?Potentially, yes, but then again, I thought McCain-Feingold was a first amendment violation.
3. The internet for the most part has remained largely free of any type of regulations whatsoever, could this be the first step in regulating this and other areas?
You bet it is, and I think the debate should perhaps center around whether this is a good thing or a bad thing. In order to do this I think we have to recognize how powerful the Internet has become. Huge amounts of money were raised for campaigns in the last election cycle over the Internet. Some directly, some indirectly, and we had a big debate about that at the time. (Wish I could find it)
If on one hand we say, the Internet is completely off-limits to FEC regulation, then folks, throw any kind of campaign finance regulation out the window. Sneaky lawyers on all sides will figure out how to use the Internet to raise unlimited amounts of money to advocate their candidates and causes. How much did Soros donate? Something like $26 million to defeat Bush? (His own words). Not picking on Soros, at least here, he was just the most obvious one. Republicans raised a ton a money too. Believe me, if the Internet is immune from campaign finance laws, they will very quickly become obsolete.
Now, if on the other hand we want to keep the FEC laws somewhat intact, it seems to me that the Internet has to be addressed in some fashion. In the most draconian sense I suppose that every post I did here during the 2004 election could have been "charged" as a campaign contribution.

Maybe not a bad idea, might have received some "invites"..... In a lesser sense perhaps someone who simply participates in online debate and has a blog that very few people pay any attention to would be exempt as long as I don't attempt to raise money for a politcal cause. There's a can of worms there though as well.....
To make this up close and personal, I would ask the question, "Where does that put America's Debate?"
Mike has ad banners here to political websites that advocate political causes. Some posters also put ads to political causes in their signatures. Does this get "charged" and counted by the FEC as a political contribution? If I include a link in a post to something at the RNC website, have I made a contribution to the RNC? On the surface it appears to be small potatoes to be sure, but when one considers how much money was raised in 2004 from the Internet, maybe it's not so small after all. It is entirely reasonable to believe that all sides could use the Internet as an end run around campaign finance laws. Whether this is a good thing or a bad thing is something to consider in this debate I think.