There are two schools of thoughts on why Operation Hilarity is not a good idea; the moral objection of using a questionable, albeit legal, tactic, and whether the tactic itself is likely to be successful. Kos is obviously a believer in the "by any legal means necessary" school of thought, so I'd rather discuss why tactically, Hilarity could possibly end up hurting the Democratic Party more than it helps.
- It's likely to increase enthusiasm within the GOP. Right now, GOP enthusiasm in the primary is about as low as it possibly could be. However, the best way to get a Republican motivated about something? Give them someone, especially the Democrats, to hate. And this is just the fodder that could get them engaged on the election. It doesn't matter if they like either candidate, once Democrats get directly involved like this, they'll become more motivated and invent reasons to support one candidate or the other just out of spite. And once someone is engaged, they're more likely to stay engaged. Which brings up the next point:
- It's likely to increase turnout in the primaries. And not just with the additional Democrats voting. Again, once the Repubs are engaged, they're more likely to turn out in support of someone, just to spite the Dems. And one of the big stories depressing the GOP right now is the decreased turnout in the primaries. Hilarity has the possiblity of taking that talking point away from us by artificially boosting turnout and giving the perception to the general public that perhaps these candidates aren't depressing motivation as much as originally thought.
- It's likely to increase turnout in the general election. Similarly to above, once you get someone engaged, they're more likely to stay engaged. So formerly demotivated Repubs will become more likely to donate time, $, or just a primary vote to someone to spite the Dems and Hilarity. And once they've emotionally invested in someone, they'll be more likely to see it through to the end.
- It cheapens the brand. There are many days and many arguments I've had regarding GOP tactics and malfeasance with others that don't follow politics closely along the lines of "both sides do it". That false equivalence haunts us in the perception of the general public, and tactics like this don't help to change that perception. And while that might not hurt President Obama specifically, it cheapens the Democratic brand and makes it tougher for those in other races, where the candidate may be less known and people are more likely to vote for party affiliation.
So tactically, Operation Hilarity comes with some big risks. That, combined with the moral objections, don't make it a path worth pursuing, in my opinion.
As a side note, we should all strive to remember that we're allies with the same ultimate goal. Name-calling and derogatory terms such as "pearl-clutching", "getting the vapors", etc., on either side, that denigrate the persons making arguments aren't helpful and have no place in what should be a reasonable discussion between individuals that ultimately should be, and should remain, on the same side in the big picture.