Has anyone mentioned the filing status yet? He should be filing as Head of Household, not Single, if he's claiming dependents! This makes a HUGE difference in tax brackets and standard deduction.

One thing I haven't seen mentioned yet is that you should also consider setting aside some money for next year's taxes even with the adjusted withholding. When you have dependents and are the sole income earner, sometimes the withholding calculations don't account for all the nuances of your specific situation. My partner and I were in a similar spot two years ago - I stayed home with our twins and he adjusted his W-4. Even though we followed all the guidance, we still ended up owing about $800 at tax time because of some credits that didn't get factored in properly to the withholding. Now we just put an extra $50-75 per month into a separate savings account as a tax buffer. It's given us so much peace of mind, and if we don't need it for taxes, it just becomes extra savings for the family. Better to be prepared than get surprised with a big bill when you're already stretching the budget with a new baby!

One practical tip I haven't seen mentioned: set up a separate bank account just for your UberEats income and expenses. I drive for multiple delivery apps and this made a HUGE difference in my tax organization. I deposit all app earnings to this account and pay for gas, repairs, etc. from it too. Makes it super easy to track your actual profit without having to sort through personal transactions. Also, save absolutely every receipt related to your deliveries - phone chargers, hot bags, trunk organizers, etc. You'd be surprised what's actually deductible.

Quick warning from someone who's been doing this for 3 years - don't forget about your state taxes too! Everyone talks about federal, but depending on your state, you might need to make estimated state tax payments as well. Also, track your TOTAL mileage for the year (personal + business) so you can calculate the business percentage accurately. So many drivers miss this and it can cause issues if you're audited.

make sure you deduct all your legitimate business expenses before calculating QBI! I'm a doctor with side consulting work and my biggest mistake first year was not tracking things like license fees, subscriptions, continuing education, malpractice insurance for the contractor work, etc. Those all reduce your taxable income which helps if your close to the threshold!

As a radiologist who's been doing contract work for several years, I can confirm you should definitely be eligible for the QBI deduction! The key thing to understand is that while radiology is considered a "specified service trade or business," you're not automatically disqualified - it just means there are income thresholds that apply. With your total income around $230,000, you'll likely qualify for at least a partial deduction depending on your filing status and final taxable income after all deductions. The phase-out for single filers starts at $182,100 and completely phases out at $232,100 for 2024 tax year. A few practical tips: Make sure you're tracking all your business expenses related to the contractor work (professional licenses, malpractice insurance, continuing education, etc.) as these reduce your taxable income. Also consider the home office deduction if you're doing reads from home - it's separate from QBI but helps reduce your overall tax burden. Don't let TurboTax's confusing interface discourage you from claiming what you're entitled to. The software sometimes makes it seem more complicated than it actually is for healthcare professionals.

This has been such a helpful discussion! As someone who's accumulated a decent amount of miles over the years and has family members who could benefit from using them, I never realized how many angles there were to consider. The consensus seems pretty clear: while the $900 should technically be reported as income for tax purposes, the bigger immediate concern is violating your airline's terms of service. I really appreciate Ellie's insider perspective on how airlines actually monitor these things - it sounds like keeping it within family and low-key is key. One thing I'm curious about that hasn't been mentioned much: what about the state tax implications? I know some states have different rules around income reporting. Would this $900 need to be reported on state returns too, or do most states just follow the federal treatment? Also, for future reference, does anyone know if the tax treatment would be different if you were transferring points from a hotel loyalty program versus airline miles? Or do the same general principles apply across all loyalty programs? Thanks again to everyone who shared their real-world experiences - this kind of practical advice is invaluable!

As a newcomer to this community, I've been following this discussion with great interest since I'm in a somewhat similar situation. My sister needs to book a last-minute flight for a family emergency, and I have more than enough miles to cover it. What I'm taking away from all the expert advice here is that while there's technically a tax obligation if money changes hands, the practical risks seem quite manageable for small family transactions. The airline policy concerns that Ellie raised are probably more important to consider in the short term. One approach I'm considering based on this discussion: I could book the flight directly for my sister using my miles, and then she could contribute to a family vacation fund or help with holiday gifts later in the year. That way there's no direct quid pro quo, but she's still able to show appreciation for the help. I really appreciate how this community breaks down complex situations with real-world experience rather than just abstract tax theory. The practical insights about airline monitoring patterns and IRS enforcement priorities are exactly the kind of information you can't find in official publications. Thanks to everyone who shared their experiences - it's given me much more confidence about how to handle this situation appropriately!

Will tax software like TurboTax handle this crypto/stock offset correctly? Or do I need something more specialized?

This is exactly the kind of situation where having proper documentation is crucial. I went through something similar last year - had about $8k in stock losses carried forward from 2022 and realized $12k in crypto gains in 2023. The good news is yes, you can absolutely offset them. Both are treated as capital assets on Schedule D. What saved me was keeping detailed records of every transaction - dates, amounts, cost basis, etc. The IRS doesn't care whether your losses came from Apple stock or your gains came from Bitcoin - they're all capital transactions. One thing to watch out for: if you're actively trading both stocks and crypto, make sure you're not running into wash sale rules. The IRS hasn't explicitly applied wash sales to crypto yet, but it's something to be aware of if you're buying and selling similar assets within 30 days. Also, since you mentioned needing an answer "ASAP" - if you're planning to realize those crypto gains before year end, consider the timing. You might want to realize them in smaller chunks to see exactly how much of your carryforward you'll use up, especially if you think you might have more gains or losses next year.