Great discussion here! I went through this exact same situation about 6 months ago when I started my corporate job while keeping my weekend Instacart deliveries. One thing I learned the hard way - don't underestimate your gig income when using any of these tools. I was conservative with my estimates and ended up owing about $800 at tax time. It's definitely better to overestimate and get a small refund than to owe money. Also, keep really good records of your gig work throughout the year. I use a simple spreadsheet to track weekly earnings from each platform, plus all my expenses (gas, car maintenance, phone mount, etc.). Makes everything so much easier when tax time comes around. The quarterly payment thing mentioned earlier is super important too. I set up automatic reminders in my phone for the due dates so I don't forget. Missing those can result in penalties even if you end up getting a refund when you file your return.

This thread has been incredibly helpful! I'm in a similar situation but with a twist - I'm starting a remote full-time job while continuing my weekend photography gig (wedding photography, not rideshare). From what I'm reading, the principles are the same regardless of the type of gig work, right? I should still use the Multiple Jobs Worksheet or the IRS estimator tool to figure out my W4, and I'll still need to make quarterly payments for the photography income since it's self-employment income with no automatic withholding. One question I have that I haven't seen addressed - does it matter that my gig work is more seasonal? Wedding season is basically March through October, so my income from photography varies dramatically throughout the year. Should I still spread the quarterly payments evenly, or adjust them to match my actual seasonal earnings? Also, thank you to everyone who shared those helpful tools and services. I've bookmarked several of them for when I inevitably get confused filling out all these forms!

Don't forget about the 529 plan payments for tuition! Those definitely count as support provided by you, not your daughter. Publication 501 specifically addresses this - educational expenses paid from a 529 plan are considered provided by the account owner (you). Also, make sure your daughter doesn't file her taxes claiming herself as her own dependent. You should coordinate with her on this to avoid any potential issues with the IRS flagging conflicting returns.

I'm an accounting student, and we just covered this in my tax class. The key distinction the IRS makes is between actual gifts versus disguised support payments. A true gift has no strings attached - you give money with no expectation of how it will be used. If you give your adult child $2,000 as a birthday present and they happen to use it for rent, that could potentially be considered their own support. But if you give money with the understanding or expectation it will be used for specific support items (like saying "here's money for your rent"), the IRS considers that as support from you, not them. The economic reality matters more than the mechanics of how the payment happens. So whether you pay the landlord directly or give your daughter money specifically for rent, both count as support from you for the support test.

Has anyone actually had the IRS question them about the time zone of a transaction? I've been trading crypto for years and report everything, but I've never been super precise about the exact time of day for transactions that happen near midnight on December 31st. I just assumed they wouldn't care about such a small detail.

This is a great question that I've actually dealt with personally! As someone who got caught in this exact situation last year with some late-night trades, I can confirm what others have said - the IRS uses your physical location's time zone when the transaction occurs. I had a similar scenario where I was in Nevada (PST) and made some Bitcoin sales on New Year's Eve around 11:45 PM. Even though it was already 2024 on the East Coast, those transactions counted for my 2023 tax year since that's where I was physically located. One thing I'd add that hasn't been mentioned - keep screenshots or records of not just the transaction itself, but also evidence of where you were. I saved my hotel receipts and flight confirmations just in case. Your exchange will show the UTC timestamp, but having proof of your location helps you convert that to the correct local time if questions ever come up. For what it's worth, most trading platforms are pretty good about this now and will show local time conversions in their tax documents, but it's always good to double-check their work, especially for those critical year-end transactions.

I just want to add that if you don't want to deal with the hassle of the ITIN application this year, you could file as "married filing separately" for now. Yes, you'll probably pay more in taxes, but it might be worth it if you need your return processed quickly. Then next year when you have more time, you can file jointly once your spouse has an ITIN or SSN. Just make sure you understand the limitations of MFS status - you lose several credits and deductions.

I went through this exact situation two years ago when I married my husband from the Philippines. Here's what worked for us: 1. Your spouse absolutely can get an ITIN - the W-7 form is still valid for spouses filing jointly. You'll need to check exception 1(d) on the form and write "Spouse of U.S. citizen/resident filing joint return" in the explanation section. 2. The tricky part is the documentation. You'll need either original documents (passport, birth certificate) or certified copies from the issuing agency (like the Philippine embassy in our case). Regular notarized copies won't work. 3. We attached the W-7 to our joint tax return and mailed everything together. The IRS processed the ITIN application first, then our return. Total time was about 10 weeks. 4. Pro tip: Double-check that your spouse qualifies as either a resident or non-resident alien for tax purposes, as this affects which exception category you select on the W-7. The IRS publication 519 has a good flowchart for this. The process is definitely still available despite what some outdated sources say. We successfully filed jointly and got our refund, just took patience with the timing. Good luck!

What tax software are most people using to handle these bank failure losses? TurboTax was confusing me last year when I tried to enter some investments that went to zero.

I'm sorry to hear about your FRC loss - that's a significant hit. One thing I'd add to the excellent advice already given is to make sure you understand the wash sale rules don't apply here since the stock became completely worthless rather than being sold and repurchased. Also, if you have any other capital gains this year, this loss can directly offset them dollar-for-dollar, which might help reduce your overall tax burden. Even if you don't have gains this year, as others mentioned, you can deduct $3,000 against ordinary income and carry the rest forward. Since you mentioned already owing taxes this year, definitely consider whether this loss might change your estimated tax payment situation. The $3,000 deduction against ordinary income could reduce what you owe by several hundred dollars depending on your tax bracket.