One more thing - if you're doing delivery driving, don't forget about quarterly estimated tax payments for 2025! Since you have self-employment income, you should be making quarterly payments to avoid penalties. I learned this the hard way my first year.

Just wanted to add that you should also consider keeping a business diary or log to document your profit motive and business activities. This can be really helpful if you ever face an audit, especially with the hobby loss rules everyone's mentioned. For your real estate work, document things like: time spent researching properties, networking events, continuing education, marketing efforts, client meetings, etc. For delivery driving, track peak hours worked, strategies to maximize earnings, vehicle maintenance schedules, etc. The IRS looks at factors like whether you operate in a businesslike manner, your expertise in the area, time and effort spent, expectation of asset appreciation, and your success in other activities. A simple log showing you're actively trying to improve profitability and treat these as real businesses (not hobbies) can go a long way. Also, since this is your first year with Schedule C, consider having a tax professional review your return before filing. The peace of mind might be worth the cost, especially given your concerns about audit risk.

Watch out for state estimated taxes too!!! Everyone's talking about federal, but depending on your state, you might need to make a state estimated payment as well. I forgot this last year when I started my side business in November and got hit with a state underpayment penalty even though I was fine on the federal side.

Just wanted to add another perspective as someone who went through this exact situation two years ago with a graduate research assistantship that started in November. One thing that really helped me was documenting everything about the timing and nature of my income for when I filed my taxes. I kept records showing that the fellowship was unavailable to me until December (had the offer letter with start date), my previous quarters' minimal income from part-time work, and calculated what my "annualized income" would have been if I tried to project the December amount across the whole year (which would have been wildly inaccurate). When I filed my return, I used Form 2210 and was able to show the IRS that requiring estimated payments based on projected annual income from a single month would have been unreasonable. The annualized income installment method completely eliminated any underpayment penalty. The key is being able to demonstrate that your income pattern was genuinely unpredictable and that making estimated payments earlier in the year based on your actual income at that time wouldn't have captured this December windfall. Keep good records and you should be fine!

Something to consider: the EITC has different income thresholds based on filing status and number of qualifying children. For 2025, with one qualifying child, EITC begins to phase out around $46,500 for single/head of household. If your sister's income is right at one of these thresholds, small changes in AGI can have a big impact on the credit amount. This might explain why you're seeing significant changes in the EITC calculation when making adjustments. Most tax software will let you try different scenarios to see what gives the best outcome. Just make sure whatever you submit is truthful - the difference between optimizing your return and misrepresenting information is a critical line you don't want to cross.

As someone who's dealt with EITC calculations for family members, I can confirm what others have said - you're absolutely allowed to choose not to claim deductions you're eligible for. The IRS doesn't require you to take every possible deduction. However, I'd strongly recommend double-checking which specific deductions are actually affecting your sister's EITC. True itemized deductions (medical expenses over 7.5% of AGI, charitable donations, etc.) shouldn't impact EITC at all since they don't change her Adjusted Gross Income. If you're seeing the EITC decrease when adding these deductions in TurboTax, there might be something else going on - perhaps some expenses are being categorized differently than you think, or there could be an interaction with other credits or calculations. Before making any decisions about skipping deductions, I'd suggest running through the calculations manually or getting a second opinion to make sure you understand exactly what's causing the EITC to change. You want to make sure you're making an informed choice rather than missing out on legitimate tax benefits due to a software quirk or misunderstanding.

I just went through this exact same process last month for my LLC's late filing penalty! You're definitely on the right track with selecting "Balance due on return or notice" - that's the correct option for penalty payments. The warning message about the tax period being out of the usual range is completely normal when you're paying an older penalty. Don't let it scare you - just click "Continue" and proceed with the payment. The system shows this warning for any tax year that's not the current or immediately previous year. A few tips from my experience: - Make sure you're logged into EFTPS with your LLC's EIN, not your personal SSN - In the reference field, enter something like "Form 1065 Late Filing Penalty 2019" to make it crystal clear what the payment is for - Print or save the confirmation page - you'll want that reference number - The payment typically processes within 1-2 business days The $2,600 amount sounds about right for a multi-year late filing penalty. Once you submit the payment, you can check your account transcript online in about a week to confirm it was applied correctly to your penalty balance.

I actually just went through this exact same situation with my LLC's 2019 Form 1065 late filing penalty a few weeks ago! You're absolutely doing it right - "Balance due on return or notice" is the correct selection for penalty payments. That warning message about the tax period being out of range is totally normal and expected when paying penalties for older tax years. The IRS system just wants to make sure you're intentionally paying for an older period. Go ahead and click "Continue" - it won't cause any issues. A couple of things that helped me get through the process smoothly: - Double-check that you're logged into EFTPS using your LLC's EIN (not your personal SSN) - In the payment reference field, I wrote "Form 1065 Late Filing Penalty - Tax Year 2019" which made it very clear what the payment was for - Keep a screenshot or printout of your confirmation page for your records The payment should process within 1-2 business days, and you can verify it was applied correctly by checking your business account transcript online after about a week. With a $2,600 penalty amount, you definitely want to make sure everything goes smoothly - but following these steps should get you there without any problems!

Just wanted to share my experience since I was in almost the exact same situation as you. I'm also waiting on my Green Card approval but have had an SSN for years and been filing taxes properly. I was really confused about that backup withholding checkbox too. I ended up calling a tax professional who confirmed what others here are saying - your immigration status doesn't matter for this specific question. Since you have an SSN and have been filing taxes without issues, you should definitely check the box saying you're NOT subject to backup withholding. The key thing to understand is that backup withholding is basically a penalty for people who haven't been compliant with tax reporting in the past. If you've been filing your returns and paying taxes properly (which it sounds like you have), then you're exempt from it regardless of whether your Green Card is still pending. Don't overthink it - just check the box and move forward with transferring your investments to Fidelity like you planned. Robinhood's sketchy practices are definitely a good reason to switch!

This whole thread has been incredibly helpful! I'm actually in a very similar situation - waiting on my Green Card but have had an SSN for about 5 years now and always filed my taxes properly. I was stressing about this same Robinhood W9 confirmation because I wasn't sure if my immigration status would affect it. Reading through everyone's responses, it's clear that backup withholding is purely about tax compliance history, not immigration status. Since I've never had any issues with the IRS and have always reported my investment income correctly, I should definitely check the box saying I'm NOT subject to backup withholding. Thanks especially to the tax professional who explained that this is essentially a penalty system for people who haven't been compliant in the past. That really cleared up my confusion. Now I can confidently handle this form and stop procrastinating on it!