Anybody have recommendations for apps to track freelance income/expenses? I'm terrible at keeping receipts and then panic at tax time lol.

As someone who also made the transition from W-2 to freelancing, I totally understand the stress! One thing that helped me a lot was opening a separate savings account specifically for taxes. Every time I get paid, I immediately transfer 30% to that account and pretend it doesn't exist. It's better to overestimate and get a refund than to scramble for money at tax time. Also, don't forget that you can make adjustments to your estimated payments throughout the year if your income changes significantly. If you have a slow quarter, you're not locked into paying the same amount - you can recalculate based on your actual income to date. The IRS Form 1040-ES has worksheets that walk you through this, and while it's not the most user-friendly, it's definitely doable once you get the hang of it. One last tip: consider making your first quarter payment a bit higher since you mentioned your income has been inconsistent. It's easier to reduce future payments if needed than to catch up if you've underpaid early in the year.

Can someone explain how CashApp Taxes handles wash sales on 1099-B forms? I have a similar merger situation but some of my trades might fall under wash sale rules.

I'm dealing with a very similar situation! My merger stocks also don't have acquisition dates on the 1099-B. Based on what everyone's saying here, it sounds like "Various" is the way to go, but I'm still nervous about getting it wrong. One thing I discovered that might help others - if you still have your original brokerage statements from before the merger, those sometimes show the original purchase dates of the stocks that got converted. I found mine buried in old PDF statements and was able to piece together the holding periods that way. Also worth noting that some mergers are tax-free reorganizations where your holding period carries over from the original stock, while others might create a new acquisition date. The type of merger matters for tax purposes, so if you're unsure, it's definitely worth getting clarification rather than guessing.

This is exactly what happened to us too! We got my husband's Letter 6419 first showing $450, then mine came about 10 days later with another $450. At first I panicked thinking we only received half of what we were supposed to get for our son. The IRS Customer Service portal at irs.gov confirmed we had received the full $900 in advance payments, just split evenly between us. When we filed jointly, we entered both amounts and everything processed smoothly. Pro tip: If you're using tax software, make sure you enter each spouse's 6419 amount in the correct field rather than just putting the total in one spot. The software needs to see how the payments were allocated between you two for proper reporting.

This happened to us as well! We received my Letter 6419 showing $600 for our two kids, but my spouse's letter didn't arrive for nearly three weeks. I was getting worried about filing deadlines. What really helped was calling the IRS using one of those callback services mentioned earlier in this thread - saved me hours of sitting on hold. The representative confirmed that married couples filing jointly do indeed get separate letters with the payments split 50/50, even if only one spouse has income. She also mentioned that if one letter gets lost in the mail, you can still file using the online portal information as long as you report the correct total amount you actually received. Just make sure your tax software has separate entry fields for each spouse's 6419 amount - don't try to combine them into one field or it might cause processing delays. For anyone still waiting on their second letter, I'd recommend checking that IRS Child Tax Credit portal first to see your total payments, then decide if you want to wait or just file with that information.

Does anyone know if there are gift tax implications for the person GIVING the stocks/crypto? I know there's an annual gift tax exclusion but I'm not sure how it applies to investments versus cash.

This is such great information! I'm actually dealing with a similar situation where my grandmother wants to gift me some mutual fund shares she's held for over 5 years. Based on what everyone's shared here, it sounds like I'd inherit her holding period, which is fantastic since I might need to sell them within the next year for graduate school expenses. One follow-up question though - does anyone know if there are any special considerations when the gift involves mutual funds versus individual stocks? I'm wondering if the dividend reinvestment over the years complicates the cost basis calculation at all, or if it's handled the same way as regular stock gifts. Also really appreciate the mentions of the various tools and services people have used - this stuff can get pretty complex and it's reassuring to know there are resources available when you need professional guidance!

Has anyone used TurboTax or other tax software to handle territorial tax situations? I'm moving to Puerto Rico next month and trying to figure out the best way to handle my taxes.

Great question about the income threshold! The $75,000 limit exists because the IRS recognizes that lower-income bona fide residents pose minimal tax compliance risk. Most tax evasion schemes involve higher amounts, so focusing resources on tracking higher earners makes sense administratively. Your approach of keeping good documentation is smart. I'd recommend maintaining: - Annual territorial tax returns - Documentation of days spent in the territory vs mainland - Employment records showing work location - Bank statements showing primary financial activity in the territory The information sharing between IRS and territorial tax authorities isn't perfect, but it does exist. If you ever get questioned, your territorial tax filing history will be your strongest defense. Since you're consistently under the threshold and filing locally, you're doing everything correctly. One thing to consider - if your income approaches $75,000 in future years, you might want to file Form 8898 voluntarily just to establish the paper trail before it becomes required.