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.
Corporations should be able to engage in political speech, as long it is done through their CEO or anyone that represents them officially, who then would be nothing more than just another citizen who happens to own a company, defending its interests. By all means, have an interesting debate, explain your point of view, reason as to why you'd like X or Y.
Money is _not_ speech. By allowing those citizens to contribute financially, in an effectively unlimited way through superPACs and other setups, you are throwing away the very foundation of democracy and equality amongst citizens when it comes to being represented.
>unions shouldn't be able to engage in political speech
Go ahead, same thing, debate! Make yourselves heard, in the streets or on television. But, once again, money can fuck right off.
There is no such foundation. You're lying to yourself. At the very least, the owners of media outlets have far more influence than other citizens due to their ability to set the conversation. There is literally nothing you can do to achieve your ridiculous ideal of equality, or to even come anywhere close to it. All you can do is change what rich people have to do to get what they want, and maybe make it more expensive. And by the way, making it more expensive just means the richest get even more of a say.
>money can fuck right off.
So I can't pay someone to build a website that (directly or indirectly) promotes a candidate?
Making yourself heard on television commonly takes the form of TV advertising, which is all about money, unfortunately.
I'm not personally convinced I know which of those two options is preferable, but those are the options. I am fairly well convinced that you can't do the latter without the former.