It's not that simple in this case, because for my first question the answer really needs to be "yes" as a clear First Amendment matter: individual political speech is clearly protected, and video is a common "speech" medium nowadays. So that's a "loophole" that is pretty much required by the Constitution.
It's really not clear to me how one can draw a sane line between the first and second question, for this case, unless you want to forbid any political video that actually takes time/effort/money to do research for (see "documentary").
And then the problem becomes that either you privilege the political speech of rich individuals over non-rich ones even more than we already do, or you have to allow non-rich individuals to pool resources to speak.
The "loophole" is then.. what exactly? What form the pooling takes? Whether the pooling is voluntary? Something else? I see a lot of people who are unhappy with the Citizens United decision, but not many proposals for what the law on this should be apart from "political speech from organizations I disagree with should not be allowed". For example, I see lots of "corporations shouldn't be able to engage in political speech" but very little of "unions shouldn't be able to engage in political speech" from Citizens United opponents. Amusingly, I see a fair amount of "unions shouldn't be able to engage in political speech" from people who support the Citizens United decision. And I have met absolutely no one who opposes the Citizens United decision and also thinks Michael Moore shouldn't be allowed to create movies in election years. Though I expect such people do exist; there just aren't many of them.