I think my income might be too high for EIC since I made about $43k at my regular job plus around $12k from deliveries. But TurboTax did guide me through a bunch of expense questions like my phone, insulated bags, and even a portion of my car insurance. I hadn't thought about tracking those things during the year but was able to go back and estimate pretty closely.

Your combined income of $55k might still qualify you for some EIC depending on your filing status. For 2022, the income limit for a single parent with one child was around $43k, but for married filing jointly it was higher. Even if you don't qualify for EIC, those business expense deductions you entered likely made a huge difference! Remember that your taxable income from the delivery work is your gross earnings minus all those business expenses. So if you made $12k but had $5k in legitimate business expenses (including that substantial mileage deduction), you're only paying taxes on $7k of additional income. If you had excess withholding from your W-2 job, that could easily result in a refund.

This is really important! I made the same mistake. Got a refund my first year doing DoorDash because my W-2 job withholding covered everything. Next year I had a $3200 tax bill that completely blindsided me. I use the IRS estimated tax payment system now (Form 1040-ES) and make quarterly payments so I don't get hit with penalties or a huge bill at tax time.

Did they ask for proof of all your expenses? I've heard they make you send bank statements and bills to prove everything on the 433-F form.

They didn't ask for proof upfront, but they did call me to verify some information. After that call, they requested three months of bank statements and copies of my utility bills and rent agreement. I think they only dig deeper if something looks inconsistent or if the amount you owe is substantial. The key is being honest on the form. If you claim expenses that are significantly higher than what the IRS considers reasonable for your area (they have internal guidelines), that will trigger more scrutiny. I stuck to my actual basic expenses and they approved my CNC status without too much back and forth.

Offers in Compromise can definitely work for offset situations, but they take time to process (6-12 months typically). If you want to stop an imminent offset, you should first request a Collection Due Process hearing to get immediate protection while you prepare your OIC. The success of an OIC depends on your financial situation. The IRS uses a specific formula to determine your "reasonable collection potential." If you can prove you'll never be able to pay the full amount before the collection statute expires (typically 10 years), you have a good chance. Form 656 is used for the offer, along with Form 433-A detailing your financial situation.

I emailed both my senators last week! One office actually responded saying the senator co-sponsored the bill to raise the married SALT cap to $20k. The more people who contact their reps, the better chance we have.

My guess is budget impact - making it permanent would show a much bigger revenue loss on the CBO score. By making it one year only, they can claim it's a smaller budget hit. Plus the whole TCJA expires after 2025 anyway, so they can just say "we'll fix it permanently when we do comprehensive tax reform"... which of course never happens lol.

Would we calculate those quarterly payments just based on our investment income or would we need to factor in possible underwithholding from our regular jobs too? And is there some calculator to figure out how much to send each quarter?

You'd want to account for both the investment income and any potential underwithholding from your jobs. The simplest approach is to take what you owed this year (your $4,300) and divide by 4 - that would be roughly $1,075 per quarter. That's assuming your income situation stays similar. There's actually a worksheet in the Form 1040-ES instructions that helps you calculate exactly what you should pay. Alternatively, if you pay at least 100% of last year's tax liability (or 110% if your AGI is over $150,000), you're generally safe from underpayment penalties even if you end up owing more when you file.

This is such a good point! My company withholds exactly 22% from bonuses regardless of my W-4 settings, and it's never enough. I always have to request additional withholding when I get my annual bonus.

Is there a specific app you recommend for keeping track of all this? I've been just taking random photos of receipts and it's a mess.

I use a combination of Google Drive for storing digital copies of forms and contracts, and then QuickBooks Self-Employed for tracking expenses, mileage, and income. The QB app lets you snap photos of receipts on the go and automatically categorizes them. For W-9s specifically, I just scan them with my phone and upload to the client's folder in Drive. I tried several expense tracking apps before settling on QuickBooks, and it's worth the monthly fee for the time it saves. Some people also like FreshBooks or Wave which are a bit simpler if you don't need all the features.

Wait so I'm confused. I did some graphic design for a company last year and filled out a W-9, but never got any tax forms from them. Should I be worried?