Quick question - do I face the same issue with multiple brokerage accounts? I have accounts with Fidelity, Robinhood and Webull, and only received 1099s from Fidelity so far.

Hey Romeo, I totally understand your stress about this! I went through something similar last year. Here's what I learned: First, check if your investment platform has a minimum threshold for issuing 1099s. Some smaller platforms only issue them if you have $10+ in dividends or $600+ in other income. With $750 in total trades, you might fall below their threshold. However, you're still legally required to report all investment income and losses regardless of whether you receive a 1099. The good news is that if you lost money overall, those losses can actually help reduce your tax burden! Here's my suggestion: Download your complete transaction history from the platform (this is usually available even if 1099s aren't). You'll need the purchase date, sale date, purchase price, and sale price for each transaction. Then you can either: 1. Use tax software that can import trading data 2. Manually fill out Form 8949 and Schedule D 3. Use one of the specialized tax tools mentioned above Don't panic about the deadline - you can always file an extension if needed. The most important thing is to report accurately, even if it means using your transaction history instead of waiting for a 1099 that might not even be coming. You've got this! The $200 loss you mentioned can actually offset other income, so it's worth documenting properly.

My sister works for the IRS (not speaking officially ofc) and she always says they have bigger fish to fry than chasing people over a few dollars. Their computer matching system might catch it, but most likely it would fall below their internal threshold for sending notices.

I'm an EA and deal with these situations regularly. For $12 in qualified dividends, you're looking at maybe $1-3 in additional tax depending on your bracket. The practical reality is that the IRS automated matching system might flag it, but it would likely fall below their enforcement threshold. That said, if you want to be 100% compliant, you can file Form 1040X. Most tax software charges around $40-60 for amendments, so you'd be paying significantly more than the actual tax owed. My recommendation for clients in similar situations: Keep the 1099-DIV with your tax records and document your decision. If you ever get a notice (highly unlikely for this amount), you can respond showing you received the document after filing and the minimal tax impact. The IRS is much more understanding when they see you have the documentation and there's clearly no intent to evade taxes.

Anyone know if Vanguard generally fixes these 1099-R issues quickly? I have a similar problem but with Fidelity and I'm getting anxious about tax deadlines approaching.

This is a really common misunderstanding with brokerages! You're absolutely correct based on the IRS rules. I work in tax compliance and see this issue frequently - the key is that recharacterizations are tied to the tax year of the original contribution, not when the transfer physically settles. Since both of your recharacterizations were for 2023 contributions and both were completed before your 2023 tax filing deadline, they should both be reported for tax year 2023. The fact that one settled in January 2024 is irrelevant. When you call Vanguard back, specifically ask for their "Retirement Services Tax Team" or "IRA Tax Specialist" rather than general customer service. Have Publication 590-A ready with the exact quotes you mentioned. Most importantly, reference the "timing" rule you cited - it's very clear that the election and transfer must both occur before the filing deadline for the contribution year. If they still push back, ask them to cite which specific IRS publication supports their position. They won't be able to because the rules are clear. Document everything in case you need to escalate to a supervisor.

Another option is using the free report from Robinhood directly. If you go to Statements & History > Tax Documents, they usually have a section for crypto transactions even if you didn't get an official 1099. You can download this and use it to fill out your 8949 manually. Worked fine for me last year. Just take your time and double-check your math.

Just to add some clarity on the reporting requirements - the IRS actually updated their stance on crypto reporting in recent years. Even if your total gains/losses are small, you're still required to answer "Yes" to the cryptocurrency question on Form 1040 if you had any crypto transactions during the year (buying, selling, exchanging, or receiving crypto as payment). The good news is that if you only had small losses, those can actually help offset other capital gains on your tax return. And if you have net capital losses, you can deduct up to $3,000 against ordinary income each year, with any excess carrying forward to future years. One tip: make sure you're tracking the exact dates and times of your transactions, especially if you bought and sold the same cryptocurrency multiple times. The IRS uses specific identification methods for determining which "lots" you sold, and this can significantly impact your tax liability. FIFO (first-in, first-out) is the default, but you can elect specific identification if you have good records.

4 Is anyone using any specific apps to track their self-employment income and expenses? I'm in a similar situation and looking for something user-friendly that won't cost a fortune.

Congratulations on your unexpected success! You're definitely not alone in this situation - many content creators find themselves in similar positions when their side hustle takes off. The good news is that not having a separate business account isn't a tax disaster. The IRS cares about accurate reporting of income and expenses, not which account they flow through. However, I'd strongly recommend opening a business account going forward to make your life much easier. A few key points for your situation: - You'll need to file Schedule C for your business income and expenses - Don't forget about self-employment tax (15.3% on net profit) - Keep detailed records of ALL income, including those large tips - Track business expenses like supplies, equipment, software subscriptions, etc. Given the complexity and your income level, hiring a CPA is probably a smart investment. They can help you get organized, ensure you're taking all allowable deductions, and set up a system for quarterly estimated payments going forward. The peace of mind and potential tax savings often more than pay for their fees. Also consider setting aside 25-30% of your earnings for taxes if you haven't been doing so already. Better to have too much saved than to be caught short at tax time!