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Don't overlook the time value of money in your calculations. If you realize $675k in gains now, assuming a 15% federal long-term capital gains rate, that's about $101k in federal taxes paid now instead of later. If you're moving in 2 years and would otherwise hold these investments for, say, another 5 years total, that's 3 years of having that $101k working for you. At a 7% annual return, that's worth around $22k in lost growth. So compare: - Pay $101k federal now = $101k total - Pay $101k federal + $32k state (4.75% of $675k) later = $133k total, but delayed 3+ years The math changes based on your actual timeline and expected returns, but don't just focus on the state tax percentage alone.
Actually, wouldn't you also need to consider what you're planning to do with the investments? If you're going to sell and then immediately rebuy similar (but not identical to avoid wash sale rules) investments, you'd get a stepped-up cost basis which could benefit you long-term.
You're absolutely right about considering the planned use of the investments. If selling and rebuying is part of the strategy (being careful with wash sale rules as you mentioned), then you'd get a stepped-up cost basis which could be valuable long-term. The stepped-up basis would be especially beneficial if you anticipate being in a higher tax bracket in the future, or if you're considering eventually passing these assets to heirs who would otherwise face significant capital gains taxes.
Has anyone considered the Alternative Minimum Tax implications here? I'm not a tax expert, but I think large capital gains can sometimes trigger AMT, which might change the math on this decision.
Good point about considering broader tax implications. For capital gains specifically, AMT doesn't usually present a major concern as capital gains are taxed at the same rate under both regular tax and AMT systems. However, large capital gains can indirectly impact AMT by increasing your overall income, which might affect AMT exemptions and adjustments. This is especially true if you have other AMT preference items like state tax deductions or certain tax credits.
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One thing nobody's mentioned yet - make sure you're tracking EVERYTHING. I use a spreadsheet with categories for all business expenses (software, equipment, home office, travel, etc). Also take photos of receipts with your phone immediately. Trust me, trying to sort through a shoebox of receipts at tax time is a nightmare I've lived through.
Do you use any specific apps for tracking expenses? I've been just using my phone's camera for receipts but it's getting disorganized fast.
I personally use QuickBooks Self-Employed which automatically categorizes most expenses when connected to your bank account/credit card. It also has a receipt scanner in the app that can match receipts to transactions. There are also free options like Wave that work well for basic tracking. The important thing is having a system - any system - rather than trying to remember everything at tax time. Just make sure you're consistent with it and do a quick review weekly so things don't pile up.
Don't forget about setting aside money for taxes! The general rule I follow is 25-30% of all freelance income goes straight into a separate savings account. Learned this the hard way my first year when I owed way more than expected. Self-employment tax (15.3%) plus regular income tax adds up fast.
I use 28% as my set-aside percentage and it's worked perfectly for the last three years. Also remember you'll need to make quarterly estimated payments if you expect to owe more than $1000 at tax time. The due dates are April 15, June 15, Sept 15, and Jan 15 of the following year.
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I had almost the identical situation with meme stocks in 2021. The key issue is "wash sales" that weren't properly reported. If you were trading the same stock multiple times within 30 days (which most of us meme stock folks were doing), the wash sale rule affects your cost basis. The brokerage SHOULD track this, but many of the discount brokers had systems that couldn't handle the volume of trades happening during that crazy period. You need to go through your trades chronologically and identify any wash sales, then adjust your cost basis accordingly. It's tedious work but you can absolutely get this fixed. The IRS is actually pretty reasonable when you can show proper documentation that proves your real gains/losses.
What software did you use to track your wash sales? I've been trying to use Excel but it's getting really complicated with hundreds of trades.
I ended up using a combination of TaxAct Premier (which has a decent stock transaction import feature) and a custom spreadsheet. The key is to sort all transactions by stock symbol and then by date, which makes it easier to identify the 30-day windows. If you have more than a hundred transactions though, I'd strongly consider using a specialized tool like the one mentioned above or hiring a tax pro who specializes in investment taxes. I spent nearly 40 hours reconstructing everything manually and still wasn't 100% confident in my calculations. It's worth paying for help with this many transactions - especially with an audit on the line.
Quick tip that helped me with a similar situation - if your IRS letter has a CP2000 number on it (check the top right corner), this isn't technically an "audit" but an automated underreporter notice. These are easier to resolve than a full audit. For CP2000 notices involving investment income, they're automatically generated when your 1099-B forms don't match what you reported. As others have said, you need to file a response with Form 8949 showing your correct cost basis. The good news is the response rate for these notices is actually pretty high if you provide proper documentation. I was in a similar situation with about $45k in "phantom gains" and got my case completely resolved within 3 months.
Yes! This is exactly right. CP2000 notices are handled by a different department than actual audits. When I called (using that phone service mentioned above), the agent confirmed that these notices are super common for the 2021 tax year because of all the trading platform issues.
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Has anyone had issues with the 1098-T not showing all qualified expenses? My wife's university didn't include some required course fees on the form even though they're eligible for the credit.
You can still claim eligible education expenses even if they're not listed on the 1098-T! Just make sure you have receipts or statements from the university showing they were required fees for enrollment. I had to do this last year for some lab fees that weren't on my 1098-T.
Just be careful with applying for the ITIN at the same time as filing. We did this last year (similar H1-B/F1 situation) and our refund was delayed nearly 4 months while they processed the ITIN application. If possible, I'd recommend getting the ITIN before filing to avoid delays.
Yikes, 4 months is a long wait! Is there any way to expedite the ITIN process? We're already in February and I'm worried about getting everything done before the filing deadline.
Unfortunately, there's no official expedite process for ITINs. However, you can use a Certified Acceptance Agent (CAA) instead of mailing in original documents, which can speed things up. Some CAAs can verify your documents on the spot and submit certified copies with your application. Also, you can still file on time even if the ITIN isn't processed yet. Just submit your return with the W-7 by the deadline, and you won't face late filing penalties. Your refund will be held until the ITIN is issued, but at least you'll be in compliance with the filing deadline.
Yuki Tanaka
This watchdog report highlights exactly why I record EVERY interaction I have with IRS personnel. You never know who you're really dealing with or what their incentives might be. I use a call recording app (legal in my state) and keep detailed notes with agent ID numbers. Also, always request written confirmation of any guidance they give you. If an agent tells you something that later turns out to be wrong, having documentation can help you avoid penalties for relying on incorrect advice.
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Esmeralda Gómez
•Is recording IRS calls legal everywhere? I'm worried about getting in trouble for that. Also, do agents actually give you their ID numbers if you ask?
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Yuki Tanaka
•Recording laws vary by state - some require two-party consent (both you and the agent) while others only require one-party consent (just you). Always check your local laws or inform the agent you're recording. IRS agents absolutely should provide their ID numbers when asked. It's typically a badge number or employee ID. I always politely say something like, "For my records, could I please have your name and ID number?" and note the date and time of the call. I've never had an agent refuse this information. If they do, that would be a red flag and worth asking to speak to a supervisor.
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Klaus Schmidt
What's shocking to me is that this isn't the first time something like this has happened. My cousin worked at the IRS in the early 2000s and said there were multiple investigations then about employees moonlighting for tax firms. The system is broken at a fundamental level.
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Aisha Patel
•I've heard similar stories. The real issue is that IRS pay isn't competitive with private sector accounting jobs, so there's always temptation. Maybe if we properly funded the agency and paid people what they're worth, we wouldn't have these ethical problems.
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