1099 NEC do I actually get tax returns and when the heck are they due??

Wait so I should have been making quarterly payments this whole time? I just got my first 1099 job in October and haven't paid anything yet. Am I going to get penalized?

For your situation starting in October, you might not face significant penalties since you've only had the income for a short period. The IRS generally assesses penalties when you've underpaid throughout the entire year. You should definitely make an estimated payment for the last quarter (January 15th deadline) to minimize any potential penalties. Going forward, plan to make quarterly estimated tax payments on April 15, June 15, September 15, and January 15 of the following year to avoid underpayment penalties.

Does it actually help with calculating those quarterly payments? That's always been the most confusing part for me.

I've tried other tax tools but they never seem to understand 1099 work properly. How is this different from something like TurboTax?

It definitely helps with calculating quarterly payments - that was actually my biggest problem before too. It gives you personalized estimates based on your specific income and deduction situation, so you know exactly how much to pay each quarter. For your question about how it's different from TurboTax, the main difference I found is that it's specifically designed for people with 1099 income rather than trying to be a one-size-fits-all solution. It automatically finds deductions that are relevant to your specific type of freelance work and explains why you qualify for them in plain English.

Wait, how exactly does this work? Does it just keep calling for you or something? I've literally spent entire afternoons on hold with the IRS.

This sounds like a scam. No way you can just magically skip the IRS hold times when millions of people are calling. What's the catch here?

It doesn't keep calling for you - they use some kind of technology that secures your place in line and then calls you when an agent is about to be available. It's similar to those restaurant services that hold your place in line and text you when your table is ready. There's no catch or scam involved. They're not claiming to have special connections at the IRS or anything shady. They just solved the technical problem of waiting on hold. I was skeptical too, but after wasting an entire day trying to get through myself, I was desperate enough to try it, and it worked exactly as promised. They called me when an agent was available, and I got my issue resolved in one day instead of spending weeks trying to get through.

Oh crap, I had no idea about this Schedule SE thing. Is the self-employment tax a lot? I made about $7,000 in the last three months from my freelance work.

The self-employment tax is approximately 15.3% of your net earnings (that's your profit after deducting business expenses). So it can definitely add up, especially if you weren't setting money aside specifically for this. For your $7,000 income, if we assume you have some business deductions that bring your net profit to around $5,500, you'd be looking at roughly $840 in self-employment tax. That's separate from any income tax you might owe. This is why many freelancers set aside 25-30% of each payment they receive - to cover both income tax and self-employment tax.

You can deduct a portion of your rent/mortgage through the home office deduction, but only if you have a space used "regularly and exclusively" for business. That's the IRS language. So if you're working from your dining table that you also eat on, that doesn't qualify. But if you have a dedicated office room or space that's only for work, you can deduct based on the percentage of your home that space takes up.