Its slightly different for freelance contractors, depending on how the business runs their shit. Bogan is not 100% talking out of her ass. Rather she is talking out of her ass, but there's a basis in fact.
tl;dr is that front page writers are freelancers who aren't paid by the hour, they are paid by the job. This absolves the company hiring them of any labor laws and taxes, and is what most companies will do because it keeps them free and clear of any taxing authorities.
So how this works is Freelancer does the job, submits an invoice, the invoice is paid and logged in the business records. When you pay an invoice, you need to have the person you're paying set up in your accounting system - this is not hard, but its a lot of form-filling and I think you have to submit all the records come tax filing time. So I can understand a normal person, let alone a work-shy faggot like Lowtax, not wanting to go through all that for someone who wrote one article and then disappeared.
I have some experience in this area, so I'm going to be autistic about it.
A good accounting practice is that any time you engage an individual to perform services for your business -- be that a self-employed lady to vacuum your office at night, a freelance writer to write articles for your shitty blog, a thot to stomp on cheeseburgers to show how serious you are about losing some fucking weight before you lose your fucking legs -- you don't pay that individual until they fill out and give you a W-9. A W-9 is a one-page IRS form that lists the individual's name, address, social security number, and signature and that's pretty much it. You then keep that form in your files. No one ever has to see it, the IRS will probably never fucking ask for it, literally nobody needs it except you.
You need it because those payments to individuals for services performed for your business are treated by the IRS as
non-employee compensation. Just like you have to report all employee compensation to the IRS on W-2s at the end of the year, you have to report non-employee compensation to the IRS as well, on a Form 1099-MISC. You don't have to send a 1099 to every motherfucker whom you chuck a $20 at,
just the people who were paid a total of $600 or more for services over the course of the year. Oh, and fishermen whom you bought more than $600 worth of fish from over the course of the year, for some fucking reason. The IRS is full of insane, nitpicky rules like that and I'm barely scratching the surface with this example. There's more, trust me. There's always more.
Any decent accounting software will help you with this. If you're keeping your books properly then every single fucking time you draw on your company's funds -- whether via check, credit card, paypal, bank wire to Nigeria, looting the petty cash box, or anything else -- you record the transaction. And any decent accounting software won't
let you record that transaction unless you type out some basic details like the date, the amount paid, and whom you paid that amount to (the "payee" in moneysperg lingo). Each payee is also treated as a distinct entity in the accounting database, to which you can attach all kinds of information such as the payee's mailing address and social security number.
Year end comes, and businesses have certain year-end responsibilities. One of these responsibilities is issuing your damn 1099s by the end of January. To do this, you query your accounting software (which
just happens to run on top of an SQL database 99% of the time and thus can take extremely specific, tailored queries) for a list of all individuals who were paid a total of $600 or more from 1/1/20XX through 12/31/20XX. Oh wait, you don't have to build a query for that because the accounting software already comes with a button or wizard that executes that exact query?
I fucking wonder why; it's almost like every single business in the United States needs to do this or something. You get your list of payees and the amounts they were paid, and unless you're fucking Uber or something there's maybe three or four people, total, who need to be issued 1099s.
Oh, and your law firm, because despite their probably being a full-fledged organization rather than an individual, you need to send them a 1099 if you paid them more than $600 because, again, random-ass rules. I could keep doing this and the post would literally never end.
So you go to Office Depot and buy a packet of blank 1099s, which costs like a few dollars and every office supply store has multiple display stands packed with them during January,
for some fucking reason. Your accounting software handles the process of printing all the required information in the right boxes on each form. The required information, by the way, is pretty much just "who was the payer, who was the payee, how much money changed hands, and what the payer and payee's social security numbers/federal tax ID numbers were." Y'know, all of the information listed on those W-9s you were supposed to obtain.
You can even get nice little 1099 envelopes with the mailing/return address windows in the right places, so you just shove the printed forms in the envelopes, lick 'em, stamp 'em, and mail 'em. The IRS also has to get a copy of each 1099 and a summary form called a 1096, but if your accounting software is good for literally anything then it'll just e-file all of that shit for you at the same time that you print the forms.
Congratulations! You're done issuing 1099s for the year. The payees receive their 1099s and use them to file their taxes, then weep at how much they owe the feds due to the self-employment tax and the fact that there's normally no withholding for 1099 payees. Literally nothing else happens unless there's something wrong with one of the 1099s you filed, which there won't be unless there was a typo or the information on those W-9s you were given was a load of horseshit. In either of those cases, you get a letter from the IRS, which basically says the following:
"Hey shithead,
One of those 1099s you filed had incorrect payee information. This could happen if the payee is trying to dodge taxes by giving you a fake social security number or fictitious name or something on their W-9 so their income won't be properly reported to us. Here's what's in our files, for comparison, assuming we have any information about that payee at all and everything he gave you wasn't just one fucking forgery."
You then get to use your own judgment. If the IRS is yelling at you because you transposed two numbers in the payee's SSN or something, just don't do that again because if you issue a second bad 1099 for the same person then there starts to be an increasing likelihood that the IRS will want to come crawl up your asshole. If the IRS's information about the payee is completely different or nonexistent compared to what you received on that W-9, you're probably going to have to start doing backup withholding, which means that every time you pay that person in the future, you're required to fork over a chunk of the money directly to the IRS. Backup withholding is shitty, annoying, and punitive by design; in practice, you're usually better off just not paying the person who's subject to backup withholding until they get their shit in order and stop lying to you on their W-9. Why are you paying that crooked asshole for anything, anyway?
So that's that. I could go a lot further into this, but it's late and I'm tired and I said I only have some experience, not all the experience. Also, none of this is to be taken as tax advice, it's just some of the shit I've dealt with. Talk to a CPA or something for that.
