Has anyone noticed that FreetaxUSA sometimes doesn't recognize the supplemental tax withholding from RSUs correctly? I had to manually add my state withholding amounts because they weren't pulling in properly from my W-2 entry.

Great thread! I'm dealing with a similar RSU situation in FreetaxUSA. One thing I discovered that might help others - if you have RSUs that vested in multiple tranches throughout the year, FreetaxUSA has a "batch entry" feature in the Capital Gains section that can save you a lot of time. Instead of entering each sale transaction individually, you can group transactions with the same acquisition date and cost basis. This is especially helpful if you had quarterly vestings and multiple same-day sales. Just make sure your total proceeds and cost basis match what's on your consolidated 1099-B. Also, for anyone wondering about ESPP (Employee Stock Purchase Plan) transactions - those follow different rules than RSUs and have their own section in FreetaxUSA under "Other Income." Don't mix them up with your RSU reporting!

I just went through this process for my 2023 taxes with our November baby, and it was much simpler than our rental property deductions! You'll need to get a Social Security Number for your baby though - the hospital will give you the paperwork, but it takes a few weeks to process. The IRS won't accept your return claiming the credit without a valid SSN for the child.

Congratulations on your upcoming bundle of joy! 🎉 As a parent who just went through this process, I can confirm that the $2,000 Child Tax Credit for 2024 is exactly right. What's great is that even though your baby arrives in June, you'll qualify for the full credit when you file your 2024 taxes next year - no proration needed! With your combined income of $185k, you're well within the safe zone. The phase-out doesn't start until $400k for married filing jointly, so you have plenty of breathing room there. One tip from my experience: start the Social Security number application process at the hospital right after birth. It typically takes 4-6 weeks to receive the card, and you'll need that SSN to claim the credit on your 2024 return. If for some reason it doesn't arrive by April 15, 2025, you can always file an extension to give yourself more time. Also, don't forget that up to $1,600 of that $2,000 credit is refundable, meaning you could get money back even if you don't owe taxes. The remaining $400 can offset any tax liability you have. It's honestly one of the more straightforward tax benefits to claim!

Check your transcript for cycle codes - those are way more important than the as of date tbh

Same thing happened to me last year - my as of date jumped around like crazy for weeks and I was losing sleep over it. Turns out it was just routine processing and I got my refund exactly when WMR originally said I would. The IRS systems are confusing but try not to stress too much about the date changes alone!

It's worth mentioning that if this is a side gig on top of your regular W-2 job, you might need to make quarterly estimated tax payments next year if you expect to owe more than $1000 in taxes from your self-employment income. You can get penalties if you wait until filing season to pay everything!

Yes, you absolutely need to report both income sources! The $950 from DoorDash and $135 from Grubhub must both be reported on your tax return, regardless of how small the amounts seem. Here's the key rule: There's NO minimum threshold for reporting self-employment income. While companies only send 1099-NEC forms when you earn $600 or more (so you might not get one from Grubhub), you're still legally required to report ALL income you receive. Since your combined total is $1,085, you'll also need to pay self-employment tax (15.3% for Social Security and Medicare) because you're over the $400 threshold. You'll report everything on Schedule C and calculate the SE tax on Schedule SE. The good news? You can deduct legitimate business expenses like mileage (67¢ per mile for 2024), portion of your phone bill, insulated bags, car chargers, etc. These deductions reduce your taxable income and can make a significant difference in what you owe. Since both gigs are delivery work, you can combine them on a single Schedule C rather than filing separate forms for each app. Keep good records of everything in case of questions later!

Great question about bonus depreciation! Just to add another perspective - I went through this exact decision last year with a $15k roof replacement. I ended up taking the bonus depreciation because my income was unusually high that year due to a consulting contract. One thing that helped me decide was running the numbers both ways. I calculated the present value of the tax savings from taking the full deduction now vs spreading it over 27.5 years. With my tax rate and the time value of money, taking it all upfront saved me about $800 in real terms. Also worth noting - if you're doing any other major improvements this year (windows, flooring, etc.), you might want to coordinate the timing. Sometimes it makes sense to bunch deductions in high-income years and spread them out in lower-income years for optimal tax planning. Your accountant will definitely want to review this when they get back, but the software isn't wrong - you do have the option!

This is such a timely question! I just went through the same decision process with a $12,000 roof replacement on my duplex. What really helped me was thinking about it from a cash flow perspective rather than just the tax savings. Since you mentioned having substantial income this year that could be offset, bonus depreciation sounds like it could work well for you. I ended up taking the full deduction because I'm in the 24% bracket this year but expecting to drop to 22% when I semi-retire in a few years. One practical tip - make sure you document WHY the roof needed to be replaced (storm damage, age, etc.) and keep photos if you have them. The IRS likes to see that improvements were necessary rather than just cosmetic upgrades, especially for larger amounts like yours. Also, don't stress too much about the decision being permanent for future improvements. Each qualifying improvement is evaluated separately, so you can always choose regular depreciation for future projects if your tax situation changes.